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1 Supporting information Access to Aminated Saturated Oxygen Heterocycles via Copper-Catalyzed Aminooxygenation of Alkenes Jian Xie, Yue-Wei Wang, Lian-Wen Qi,* and Bo Zhang* State Key Laboratory of Natural Medicines, China armaceutical University, 24 Tongjia Xiang, Nanjing , China Table of contents General Optimization of reaction conditions Results for copper-catalyzed intermolecular aminooxygenation of alkenes General procedure for the preparation of 2-vinylbenzoic acids General procedure for the preparation of alcohols General procedure for copper-catalyzed aminooxygenation of alkenes (GP) ysical data of the compounds Lager scale experiment Mechanistic studies Crystallographic data of 2a References NMR spectra S2 S3 S4 S4 S5 S5 S5 S17 S18 S20 S21 S22 S1

2 General All manipulations were conducted with a standard Schlenk tube under a nitrogen atmosphere. Unless otherwise noted, materials obtained from commercial suppliers were used without further purification. Flash column chromatography was carried out on silica gel ( mesh). Thin layer chromatography (TLC) was performed using silica gel 60 F 254 plates. 1 H NMR spectra were recorded on a Bruker AV-300 spectrometer at room temperature. Chemical shifts (in ppm) were referenced to tetramethylsilane (δ = 0 ppm) in CDCl 3 as an internal standard. 13 C NMR spectra were obtained by the same NMR spectrometer and were calibrated with CDCl 3 (δ = ppm). Data for 1 H NMR are reported as follows: chemical shifts (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet or unresolved, br s = broad singlet), coupling constant (Hz) and integration. Data for 13 C NMR are reported in terms of chemical shift and multiplicity where appropriate. Mass spectra were performed on an Aglient 6530 Q-TOF for HRMS. The yields were determined on a METTLER TOLEDO ME 104 balance (accuracy: 0.1 mg). Melting points (Mp) were determined on a SGW X-4B and are uncorrected. Carboxylic acid 1a-g were prepared according to the reported method. [1] Carboxylic acids 1h-k and 1m were prepared according to the reported method. [2] Carboxylic acid 1l was prepared according to the reported method. [3] Alcohols 1n-q were prepared according to the reported method. [3,4] Amides 1r and 1s were prepared according to the reported method. [5] Amide 1t was prepared according to the reported method. [6] Internal alkene (E)-1u was prepared according to the reported method. [7] Internal alkene (E)-1v was prepared according to the reported method. [8] Internal alkene (Z)-1u and (Z)-1v were prepared according to the reported method. [9] S2

3 Optimization of reaction conditions Table S1. Base screening a a Reaction conditions: 1a (0.2 mmol), CuCl (10 mol %), L2 (10 mol %), base (0.4 mmol), and NFSI (0.3 mmol) in DCE (1.5 ml) at 70 o C under N 2 for 6 h. b Isolated yields. S3

4 Results for copper-catalyzed intermolecular aminooxygenation of alkenes: a Reaction conditions: 1' (0.2 mmol), 2' (0.3 mmol), CuCl (10 mol %), L2 (10 mol %), and NFSI (0.3 mmol) in DCE (1.5 ml) at 70 o C under N 2 for 6 h. General procedure for the preparation of 2-vinylbenzoic acids: To a suspension of methyltriphenylphophonium bromide (5.0 mmol, 1.0 equiv) in THF (25.0 ml) was added potassium tert-butoxide (7.5 mmol, 1.5 equiv). The resulting yellow solution was stirred at room temperature for 1.5 h. Acid (5.0 mmol, 1.0 equiv) was added to the reaction mixture. After the solution was refluxed overnight, the reaction mixture was cooled to room temperature and quenched with acetic acid (1.5 ml), followed by addition of EtOAc (25.0 ml). The organic layer was extracted with a saturated aqueous solution of NaHCO 3 (30.0 mlx3). The combined aqueous layers were acidified to ph 1 with concentrated HCl and the organic layer extracted with EtOAc (50.0 mlx3). The combined organic layer was dried over anhydrous Na 2 SO 4, filtered, and concentrated by rotary evaporation. The crude reaction mixture was purified by flash column chromatography on silica gel to afford the corresponding product. S4

5 General procedure for the preparation of alcohols: To a cooled (0 C) suspension of lithium aluminum hydride (12.5 mmol, 2.5 equiv) in Et 2 O (30.0 ml) was added dropwise a solution of the corresponding acids (5.0 mmol, 1.0 equiv) in Et 2 O (20.0 ml). After 5 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 5 h. The mixture was re-cooled to 0 C and aq. sat. potassium sodium tartrate (25.0 ml) added slowly. The biphasic mixture was allowed to stir at room temperature for 20 h then extracted with Et 2 O (30.0 mlx3). The combined organic layer was washed with water (50.0 ml), dried over anhydrous Na 2 SO 4, filtered, and concentrated in vacuo. The crude reaction mixture was purified by flash column chromatography on silica gel to afford the corresponding product. General procedure for copper-catalyzed aminooxygenation of alkenes (GP): Alkene 1 (0.2 mmol, 1.0 equiv), NFSI (0.3 mmol, 1.5 equiv), CuCl (0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (0.02 mmol, 0.1 equiv) were placed in a dry 10 ml Schlenk tube under a nitrogen atmosphere. DCE (1.5 ml) was added with a syringe and the reaction mixture was stirred at 70 o C for 6 h monitored with TLC. After completion of the reaction, it was cooled to room temperature and transferred to a round-bottomed flask after dilution with CH 2 Cl 2. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel to afford the product. ysical data of the compounds N-((1-methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)be nzenesulfonamide (2a) According to GP with 2-(prop-1-en-2-yl)benzoic acid 1a (32.5 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude S5

6 reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2a as white solid (72.9 mg, 80%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), (m, 3H), (m, 6H), 4.34 (d, J = 16.2 Hz, 1H), 4.17 (d, J = 16.2 Hz, 1H), 1.53 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 168.6, 151.0, 139.7, 134.3, 134.0, 129.8, 128.9, 128.8, 126.1, 125.9, 121.9, 86.1, 56.4, 23.4; HRMS (ESI) calculated for C 22 H 20 NO 6 S 2 [M+H] + m/z , found N-((1-ethyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)benz enesulfonamide (2b) According to GP with 2-(but-1-en-2-yl)benzoic acid 1b (35.3 mg, 0.2 mmol, 1.0 equiv), NFSI (95.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2b as white solid (66.1 mg, 70%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), (m, 3H), (m, 6H), 4.39 (d, J = 16.2 Hz, 1H), 4.24 (d, J = 16.2 Hz, 1H), (m, 2H), 0.41 (d, J = 7.2 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 168.9, 148.9, 139.5, 134.1, 133.9, 129.7, 128.9, 128.7, 127.3, 125.6, 122.2, 88.7, 55.9, 28.5, 6.5; HRMS (ESI) calculated for C 23 H 22 NO 6 S 2 [M+H] + m/z , found N-((1-cyclohexyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl )benzenesulfonamide (2c) According to GP with 2-(1-cyclohexylvinyl)benzoic acid 1c (46.7 mg, 0.2 mmol, 1.0 S6

7 equiv), NFSI (107.2 mg, 0.34 mmol, 1.7 equiv), CuCl (2.4 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1-5/1) to afford the desired product 2c as white solid (50.1 mg, 48%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 5H), (m, 5H), 4.50 (s, 2H), (m, 1H), (m, 4H), (m, 1H), (m, 2H), (m, 2H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 169.2, 147.9, 139.2, 133.8, 133.2, 129.2, 128.9, 128.4, 127.6, 125.2, 124.2, 89.9, 52.7, 45.6, 27.1, 26.3, 26.0, 25.9, 25.8; HRMS (ESI) calculated for C 27 H 28 NO 6 S 2 [M+H] + m/z , found N-((3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)benzenesulf onamide (2d) According to GP with 2-vinylbenzoic acid 1d (30.0 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.2 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.8 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 50/1) to afford the desired product 2d as white solid (36.9 mg, 42%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), (m, 3H), (m, 6H), 5.81 (dd, J = 8.4, 3.3 Hz, 1H), 4.13 (dd, J = 16.0, 3.3 Hz, 1H), 4.02 (dd, J = 16.0, 3.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 169.2, 146.0, 139.1, , , 130.0, 129.1, 128.7, 126.1, 126.0, 122.5, 79.9, 52.5; HRMS (ESI) calculated for C 21 H 18 NO 6 S 2 [M+H] + m/z , found S7

8 N-((3-oxo-1-phenyl-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)be nzenesulfonamide (2e) According to GP with 2-(1-phenylvinyl)benzoic acid 1e (45.3 mg, 0.2 mmol, 1.0 equiv), NFSI (95.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (5.0 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2e as white solid (55.0 mg, 53%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 4H), (m, 2H), (m, 4H), (m, 5H), (m, 3H), 4.75 (s, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 168.4, 148.7, 139.2, 138.6, 133.8, 129.7, 129.6, 128.9, 128.7, 128.6, 128.3, 126.0, 125.5, 125.2, 124.5, 88.2, 55.8; HRMS (ESI) calculated for C 27 H 22 NO 6 S 2 [M+H] + m/z , found N-((3-oxo-1-(p-tolyl)-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)b enzenesulfonamide (2f) According to GP with 2-(1-(p-tolyl)vinyl)benzoic acid 1f (48.0 mg, 0.2 mmol, 1.0 equiv), NFSI (95.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (5.0 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2f as white solid (48.1 mg, 45%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 4H), (m, 2H), (m, 2H), (m, 7H), (m, 2H), 4.73 (s, 2H), 2.29 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 168.5, 148.8, 139.3, 138.6, 135.7, 133.7, 129.5, 129.3, 128.9, 128.3, 126.1, 125.5, 125.2, 124.5, 88.3, 55.7, 20.9; HRMS S8

9 (ESI) calculated for C 28 H 24 NO 6 S 2 [M+H] + m/z , found N-((1-(4-chlorophenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenyls ulfonyl)benzenesulfonamide (2g) According to GP with 2-(1-(4-chlorophenyl)vinyl)benzoic acid 1g (52.0 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (3.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.5 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 20/1) to afford the desired product 2g as white solid (63.0 mg, 57%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 5H), (m, 2H), (m, 2H), (m, 7H), (m, 2H), 4.69 (q, J = 16.3 Hz, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 168.2, 148.5, 139.3, 137.0, 134.8, 134.1, 133.9, 129.9, 129.0, 128.9, 128.4, 127.0, 126.0, 125.9, 124.2, 87.8, 55.9; HRMS (ESI) calculated for C 27 H 21 ClNO 6 S 2 [M+H] + m/z , found N-((5-oxo-2-phenyltetrahydrofuran-2-yl)methyl)-N-(phenylsulfonyl)benzenesulfo namide (2h) According to GP with 4-phenylpent-4-enoic acid 1h (35.5 mg, 0.2 mmol, 1.0 equiv), NFSI (95.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.6 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 20/1) to afford the desired product 2h as white solid (63.2 mg, 67%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 5H), 4.53 (d, J = 16.8 Hz, 1H), 4.15 (d, J = 16.8 Hz, 1H), (m, 2H), (m, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ S9

10 175.0, 140.4, 139.6, 134.0, 129.2, 128.9, 128.6, 128.5, 125.2, 88.7, 56.8, 31.6, 28.0; HRMS (ESI) calculated for C 23 H 22 NO 6 S 2 [M+H] + m/z , found N-((4,4-dimethyl-5-oxo-2-phenyltetrahydrofuran-2-yl)methyl)-N-(phenylsulfonyl )benzenesulfonamide (2i) According to GP with 2,2-dimethyl-4-phenylpent-4-enoic acid 1i (43.2 mg, 0.2 mmol, 1.0 equiv), NFSI (94.3 mg, 0.3 mmol, 1.5 equiv), CuCl (2.2 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2i as white solid (40.3 mg, 40%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 5H), 4.51 (d, J = 16.7 Hz, 1H), 4.07 (d, J = 16.7 Hz, 1H), (m, 2H), 0.67 (d, J = 12.9 Hz, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 180.3, 142.1, 139.8, 134.0, 129.2, 128.9, 128.6, 128.4, 125.2, 85.6, 57.6, 45.0, 40.0, 26.1, 24.8; HRMS (ESI) calculated for C 25 H 26 NO 6 S 2 [M+H] + m/z , found N-((2-methyl-5-oxo-4,4-diphenyltetrahydrofuran-2-yl)methyl)-N-(phenylsulfonyl )benzenesulfonamide (2j) According to GP with 4-methyl-2,2-diphenylpent-4-enoic acid 1j (54.0 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 15/1) to afford the desired product 2j as white solid (80.6 mg, 72%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), S10

11 (m, 2H), (m, 4H), (m, 4H), (m, 4H), (m, 2H), 4.22 (d, J = 16.4 Hz, 1H), 3.98 (d, J = 16.4 Hz, 1H), 3.16 (d, J = 13.8 Hz, 1H), 2.94 (d, J = 13.8 Hz, 1H), 1.14 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 175.6, 142.5, 141.9, 139.6, 133.9, 128.9, 128.8, 128.5, 128.4, , , 127.2, 127.0, 82.6, 57.7, 56.4, 45.2, 24.7; HRMS (ESI) calculated for C 30 H 28 NO 6 S 2 [M+H] + m/z , found N-((6-oxo-2-phenyltetrahydro-2H-pyran-2-yl)methyl)-N-(phenylsulfonyl)benzene sulfonamide (2k) According to GP with 5-phenylhex-5-enoic acid 1k (38.0 mg, 0.2 mmol, 1.0 equiv), NFSI (95.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 20/1) to afford the desired product 2k as white solid (46.3 mg, 48%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 4H), (m, 1H), 4.38 (d, J = 16.5 Hz, 1H), 4.23 (d, J = 16.5 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 170.4, 141.1, 140.1, 133.8, 129.0, 128.5, 128.3, 125.5, 87.9, 60.0, 29.0, 28.5, 15.8; HRMS (ESI) calculated for C 24 H 24 NO 6 S 2 [M+H] + m/z , found N-((3-methyl-1-oxoisochroman-3-yl)methyl)-N-(phenylsulfonyl)benzenesulfonam ide (2l) According to GP with 2-(2-methylallyl)benzoic acid 1l (35.2 mg, 0.2 mmol, 1.0 equiv), NFSI (95.2 mg, 0.3 mmol, 1.5 equiv), CuCl (2.3 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum S11

12 ether/etoac = 30/1-3/1) to afford the desired product 2l as white solid (84.6 mg, 90%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), 8.01 (d, J = 7.7 Hz, 1H), (m, 7H), (m, 1H), 7.19 (d, J = 7.7 Hz, 1H), 4.20 (s, 2H), 3.10 (d, J = 16.4 Hz, 1H), 2.95 (d, J = 16.4 Hz, 1H), 1.33 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 163.4, 139.7, 137.0, , , 129.9, 128.9, 128.7, 128.1, 127.6, 124.2, 82.2, 56.8, 35.7, 23.4; HRMS (ESI) calculated for C 23 H 22 NO 6 S 2 [M+H] + m/z , found N-((7-oxo-2-phenyloxepan-2-yl)methyl)-N-(phenylsulfonyl)benzenesulfonamide (2m) According to GP with 6-phenylhept-6-enoic acid 1m (49.7 mg, 0.2 mmol, 1.0 equiv), NFSI (94.4 mg, 0.3 mmol, 1.5 equiv), CuCl (1.9 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.0 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 25/1-16/1) to afford the desired product 2m as white solid (24.6 mg, 25%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 2H), (m, 3H), 4.40 (d, J = 15.6 Hz, 1H), 4.01 (d, J = 15.9 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 173.8, 140.4, 139.7, 133.6, 129.4, 128.8, 128.4, 126.0, 86.4, 62.6, 37.0, 32.5, 23.6, 22.4; HRMS (ESI) calculated for C 25 H 26 NO 6 S 2 [M+H] + m/z , found N-((1-methyl-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsulfonyl)benzenes ulfonamide (2n) According to GP with (2-(prop-1-en-2-yl)phenyl)methanol 1n (30.9 mg, 0.2 mmol, 1.0 equiv), NFSI (126.1 mg, 0.4 mmol, 2.0 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.3 mg, 0.02 mmol, 0.1 equiv). The S12

13 crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 30/1) to afford the desired product 2n as white solid (18.3 mg, 21%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 3H), (m, 1H), 4.94 (s, 2H), 4.15 (d, J = 15.6 Hz, 1H), 3.95 (d, J = 15.6 Hz, 1H), 1.46 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 143.1, 140.6, 139.7, 133.5, 128.7, 128.5, 128.2, 127.5, 121.5, 121.2, 87.4, 70.6, 56.1, 23.9; HRMS (ESI) calculated for C 22 H 22 NO 5 S 2 [M+H] + m/z , found N-(phenylsulfonyl)-N-((2-phenyltetrahydrofuran-2-yl)methyl)benzenesulfonamid e (2o) According to GP with 4-phenylpent-4-en-1-ol 1o (35.8 mg, 0.2 mmol, 1.0 equiv), NFSI (96.1 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.1 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 30/1) to afford the desired product 2o as white solid (67.3 mg, 74%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 6H), (m, 2H), (m, 2H), (m, 1H), 4.34 (d, J = 16.1 Hz, 1H), 4.10 (d, J = 16.1 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 143.4, 140.9, 133.4, 128.7, , , 127.3, 125.6, 87.2, 65.3, 57.2, 33.6, 24.1; HRMS (ESI) calculated for C 23 H 24 NO 5 S 2 [M+H] + m/z , found N-((2-methyl-4,4-diphenyltetrahydrofuran-2-yl)methyl)-N-(phenylsulfonyl)benze nesulfonamide (2p) According to GP with 4-methyl-2,2-diphenylpent-4-en-1-ol 1p (51.9 mg, 0.2 mmol, 1.0 equiv), NFSI (94.1 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The S13

14 crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 30/1) to afford the desired product 2p as white solid (27.0 mg, 25%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 10H), 4.47 (d, J = 9.3 Hz, 1H), (m, 2H), 3.73 (d, J = 15.6 Hz, 1H), 2.71 (d, J = 12.9 Hz, 1H), 2.56 (d, J = 12.9 Hz, 1H), 1.07 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 146.7, 146.2, 140.3, 133.5, 128.6, 128.5, 128.4, 128.3, 127.1, 127.0, 126.2, 126.1, 83.3, 75.3, 56.3, 56.0, 49.0, 24.6; HRMS (ESI) calculated for C 30 H 30 NO 5 S 2 [M+H] + m/z , found N-(phenylsulfonyl)-N-((2-phenyltetrahydro-2H-pyran-2-yl)methyl)benzenesulfon amide (2q) According to GP with 5-phenylhex-5-en-1-ol 1q (36.3 mg, 0.2 mmol, 1.0 equiv), NFSI (94.2 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.3 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 30/1) to afford the desired product 2q as white solid (47.8 mg, 51%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 4H), (m, 1H), 4.16 (d, J = 15.6 Hz, 1H), 3.84 (d, J = 15.6 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 141.5, 140.2, 133.2, 128.7, 128.5, 128.3, 127.5, 127.1, 79.3, 62.0, 61.1, 28.5, 24.6, 19.0; HRMS (ESI) calculated for C 24 H 26 NO 5 S 2 [M+H] + m/z , found N-((1-methyl-3-(tosylimino)-1,3-dihydroisobenzofuran-1-yl)methyl)-N-(phenylsul fonyl)benzenesulfonamide (2r) S14

15 According to GP with 2-(prop-1-en-2-yl)-N-tosylbenzamide 1r (64.5 mg, 0.2 mmol, 1.0 equiv), NFSI (95.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.2 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.4 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 6/1) to afford the desired product 2r as white solid (38.7 mg, 32%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 6H), (m, 1H), (m, 3H), (m, 6H), (m, 2H), 4.38 (d, J = 17.1 Hz, 1H), 4.28 (d, J = 16.8 Hz, 1H), 2.41 (m, 3H), 1.55 (m, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 165.5, 149.6, 143.3, , , 134.9, 134.2, 130.0, 129.2, 128.8, 127.5, 125.7, 121.8, 95.1, 56.1, 23.8, 21.5; HRMS (ESI) calculated for C 29 H 27 N 2 O 7 S 3 [M+H] + m/z , found N-((3-methyl-1-(tosylimino)isochroman-3-yl)methyl)-N-(phenylsulfonyl)benzenes ulfonamide (2s) According to GP with 2-(2-methylallyl)-N-tosylbenzamide 1s (66.5 mg, 0.2 mmol, 1.0 equiv), NFSI (96.0 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 20/1-5/1) to afford the desired product 2s as white solid (49.6 mg, 40%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.13 (d, J = 7.8 Hz, 1H), (m, 6H), (m, 2H), (m, 5H), (m, 3H), 7.10 (d, J = 7.5 Hz, 1H), 4.17 (d, J = 16.7 Hz, 1H), 3.94 (d, J = 16.7 Hz, 1H), 3.02 (d, J = 16.8 Hz, 1H), 2.88 (d, J = 16.8 Hz, 1H), 2.40 (s, 3H), 1.00 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 160.7, 143.1, 139.2, 138.8, 135.9, 134.5, 134.1, 129.5, 129.0, 128.9, 128.7, 128.5, 127.6, 127.4, 123.3, 85.4, 55.9, 34.3, 23.1, 21.4; HRMS (ESI) calculated for C 30 H 29 N 2 O 7 S 3 [M+H] + m/z , found S15

16 N-((2,5-diphenyl-4,5-dihydrooxazol-5-yl)methyl)-N-(phenylsulfonyl)benzenesulfo namide (2t) According to GP with N-(2-phenylallyl)benzamide 1t (47.6 mg, 0.2 mmol, 1.0 equiv), NFSI (94.5 mg, 0.3 mmol, 1.5 equiv), CuCl (2.2 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 12/1-8/1) to afford the desired product 2t as white solid (43.5 mg, 41%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 2H), (m, 5H), (m, 7H), 4.75 (d, J = 16.8 Hz, 1H), 4.46 (d, J = 15.6 Hz, 1H), 4.29 (d, J = 16.8 Hz, 1H), 4.18 (d, J = 15.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 161.8, 142.7, 139.7, 133.7, 131.4, 128.8, 128.6, 128.3, 128.2, 128.1, 128.0, 127.5, 124.7, 89.2, 64.0, 56.0; HRMS (ESI) calculated for C 28 H 25 N 2 O 5 S 2 [M+H] + m/z , found N-((2S*,3R*)-5-oxo-2-phenyltetrahydrofuran-3-yl)-N-(phenylsulfonyl)benzenesul fonamide (2u) According to GP with (E)-4-phenylbut-3-enoic acid (E)-1u (32.4 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 20/1-10/1) to afford the desired product 2u as white solid (48.6 mg, 53%). When (Z)-4-phenylbut-3-enoic acid (Z)-1u (32.6 mg, 0.2 mmol, 1.0 equiv) was used as starting material, 2u was obtained in 46% yield (41.7 mg). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 3H), (m, 2H), 5.82 (d, J = 5.6 Hz, 1H), 4.95 (dt, J = 10.4, 5.6 Hz, 1H), 3.04 (dd, J = 18.1, 5.6 Hz, 1H), 2.83 (dd, J = 18.1, 10.4 Hz, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 172.8, 139.2, 137.3, 134.4, 129.3, 129.0, 128.9, 128.1, S16

17 125.4, 83.5, 63.2, 33.6; HRMS (ESI) calculated for C 22 H 20 NO 6 S 2 [M+H] + m/z , found N-(phenylsulfonyl)-N-((2S*,3R*)-2-phenyltetrahydrofuran-3-yl)benzenesulfonam ide (2v) According to GP with (E)-4-phenylbut-3-en-1-ol (E)-1v (30.1 mg, 0.2 mmol, 1.0 equiv), NFSI (94.2 mg, 0.3 mmol, 1.5 equiv), CuCl (2.1 mg, 0.02 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline (4.2 mg, 0.02 mmol, 0.1 equiv). The crude reaction mixture was purified by flash silica gel column chromatography (petroleum ether/etoac = 30/1-15/1) to afford the desired product 2v as colourless oil (50.5 mg, 57%). When (Z)-4-phenylbut-3-en-1-ol (Z)-1v (30.2 mg, 0.2 mmol, 1.0 equiv) was used as starting material, 2v was obtained in 49% yield (43.0 mg). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 5H), 5.34 (d, J = 7.8 Hz, 1H), 4.64 (dt, J = 10.0, 7.5 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 140.0, 139.0, 133.8, 129.0, 128.5, 128.2, 128.1, 126.4, 80.7, 67.9, 67.0, 30.9; HRMS (ESI) calculated for C 22 H 22 NO 5 S 2 [M+H] + m/z , found Lager scale experiment 2-(Prop-1-en-2-yl)benzoic acid 1a (0.65 g, 4.0 mmol, 1.0 equiv), NFSI (1.89 g, 6.0 mmol, 1.5 equiv), CuCl (40.3 mg, 0.4 mmol, 0.1 equiv), and 2,9-dimethyl-1,10-phenanthroline L2 (84.0 mg, 0.4 mmol, 0.1 equiv) were placed in a 100 ml round bottom flask under a nitrogen atmosphere. DCE (30.0 ml) was added with a syringe and the reaction mixture was stirred at 70 o C for 6 h. After completion of the reaction, it was cooled to room temperature and transferred to a round-bottomed flask after dilution with CH 2 Cl 2. The solvent was removed under S17

18 reduced pressure and the residue was purified by flash column chromatography (petroleum ether/etoac = 25/1) to afford the desired product 2a as white solid (1.24 g, 68%). Mechanistic studies Radical inhibition experiments: 2-(Prop-1-en-2-yl)benzoic acid 1a (33.1 mg, 0.2 mmol, 1.0 equiv), NFSI (94.1 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), 2,9-dimethyl-1,10-phenanthroline L2 (4.2 mg, 0.02 mmol, 0.1 equiv), and 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) (63.4 mg, 0.4 mmol, 2.0 equiv) were placed in a dry 10 ml Schlenk tube under a nitrogen atmosphere. DCE (1.5 ml) was added with a syringe and the reaction mixture was stirred at 70 o C for 6 h. The formation of 2a was completely suppressed. 2-(Prop-1-en-2-yl)benzoic acid 1a (33.2 mg, 0.2 mmol, 1.0 equiv), NFSI (94.5 mg, 0.3 mmol, 1.5 equiv), CuCl (2.2 mg, 0.02 mmol, 0.1 equiv), 2,9-dimethyl-1,10-phenanthroline L2 (4.2 mg, 0.02 mmol, 0.1 equiv), and 2,6-di-tert-butyl-4-methylphenol (BHT) (88.1 mg, 0.4 mmol, 2.0 equiv) were placed in a dry 10 ml Schlenk tube under a nitrogen atmosphere. DCE (1.5 ml) was added with a syringe and the reaction mixture was stirred at 70 o C for 6 h. The formation of 2a was completely suppressed. S18

19 Radical capture experiment: 2-(Prop-1-en-2-yl)benzoic acid 1a (33.0 mg, 0.2 mmol, 1.0 equiv), NFSI (94.6 mg, 0.3 mmol, 1.5 equiv), CuCl (2.0 mg, 0.02 mmol, 0.1 equiv), 2,9-dimethyl-1,10-phenanthroline L2 (4.2 mg, 0.02 mmol, 0.1 equiv), and ethene-1,1-diyldibenzene (36.5 mg, 0.2 mmol, 1.0 equiv) were placed in a dry 10 ml Schlenk tube under a nitrogen atmosphere. DCE (1.5 ml) was added with a syringe and the reaction mixture was stirred at 70 o C for 6 h monitored with TLC. After completion of the reaction, it was cooled to room temperature and transferred to a round-bottomed flask after dilution with CH 2 Cl 2. The solvent was removed under reduced pressure and the residue was purified by flash silica gel column chromatography (petroleum ether/et 2 O = 15/1) to afford the product 3 as white solid (85.2 mg, 90%). Mp: C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 4H), (m, 3H), (m, 7H), 6.14 (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 152.1, 139.7, 138.5, 136.6, 133.7, 129.7, 129.0, 128.7, , , 128.3, 128.2, 128.0, 116.2; HRMS (ESI) calculated for C 26 H 22 NO 4 S 2 [M+H] + m/z , found Analytical data are in agreement with those reported in the literature. [10] S19

20 Crystallographic data of 2a S20

21 References: [1] (a) Song, S.; Zhu, S.-F.; Yu, Y.-B.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2013, 52, (b) Bunescu, A.; Wang, Q.; Zhu, J. Chem. Eur. J. 2014, 20, (c) Yang, S.; Zhu, S.-F.; Guo, N.; Song, S.; Zhou, Q.-L. Org. Biomol. Chem. 2014, 12, [2] (a) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, (b) Zhu, R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2013, 52, [3] Hewitt, J. F. M.; Williams, L.; Aggarwal, P.; Smith, C. D.; France, D. J. Chem. Sci. 2013, 4, [4] (a) Ha, T. M.; Wang, Q.; Zhu, J. Chem. Commun. 2016, 52, (b) Gao, Y.; Li, X.; Chen, W.; Tang, G.; Zhao, Y. J. Org. Chem. 2015, 80, [5] Zhao, J.-F.; Duan, X.-H.; Yang, H.; Guo, L.-N. J. Org. Chem. 2015, 80, [6] Deng, Q.-H.; Chen, J.-R.; Wei, Q.; Zhao, Q.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Commun. 2015, 51, [7] Yasu, Y.; Arai, Y.; Tomita, R.; Koike, T.; Akita, M. Org. Lett. 2014, 16, 780. [8] Lin, R.; Sun, H.; Yang, C.; Shen, W.; Xia, W. Chem. Commun. 2015, 51, 399. [9] Denmark, S. E.; Collins, W. R. Org. Lett. 2007, 9, [10] Li, Y.; Hartmann, M.; Daniliuc, C. G.; Studer, A. Chem. Commun. 2015, 51, S21

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63 S63

64 Hb From (E)-1u: Ha S64

65 From (E)-1u: S65

66 Hb From (Z)-1u: Ha S66

67 From (Z)-1u: S67

68 S68

69 S69

70 Hb From (E)-1v: Ha S70

71 From (E)-1v: S71

72 Hb From (Z)-1v: Ha S72

73 From (Z)-1v: S73

74 S74

75 S75

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