Supporting Information. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation. of Sulfoxonium Ylides. Xingwei Li*, Table of Contents

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1 Supporting Information Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides Youwei Xu,, Xifa Yang,, Xukai Zhou,, Lingheng Kong,, and Xingwei Li*, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian , China University of Chinese Academy of Sciences, Beijing , China Table of Contents I. General Information... S2 II. Synthesis of Substrates... S2 (a) General procedure for preparation of sulfoxonium ylides... S2 (b) General procedures for the reaction... S2 III. Characterization Data... S3 IV. Gram-Scale Preparation and Transformations... S13 (a) Gram-Scale Preparation of 3aa... S13 (b) Transformations of 3aa... S14 V. Mechanistic Studies... S15 VI. References... S17 VII. NMR Spectra of Products... S18 S1

2 I. General Information All chemicals were obtained from commercial sources and were used as received unless otherwise noted. All reactions were carried out using Schlenk techniques or in a nitrogen-filled glove box in absolute ethanol. NMR Spectra were recorded on a 400 MHz NMR spectrometer in the solvent indicated. The chemical shift is given in dimensionless δ values and is frequency referenced relative to TMS in 1 H and 13 C NMR spectroscopy. The following abbreviations were used to describe peak splitting patterns when appropriate: br = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = double of doublet, dt = double of triplet, td = triple of doublet. HRMS data were obtained via ESI mode with TOF mass analyzer. Column chromatography was performed on silica gel ( mesh) using ethyl acetate (EA)/petroleum ether (PE). II. Synthesis of Substrates (a) General procedure for preparation of sulfoxonium ylides Ylides 1a-1p were prepared according to the reported procedures. 1 To a stirred solution of potassium tert-butoxide (3.0 g, 27.2 mmol) in THF (30 ml) was added trimethylsulfoxonium iodide (5.0 g, 20.6 mmol) at room temperature. The resulting mixture is refluxed for 2h. Then reaction mixture is cooled to 0 C, followed by addition of acyl chlorides (7 mmol) in THF (5 ml). The reaction was allowed to room temperature and stirred for 3h. Next, the solvent was evaporated and water (15 ml) and ethyl acetate (20 ml) were added to the resulting slurry. The layers were separated and the aqueous layer was washed with ethyl acetate (2 x 30 ml) and the organic layers were combined. The organic solution was dried over anhydrous sodium sulphate (Na 2SO 4), filtered over a sintered funnel and evaporated to dryness. The crude product was purified by flash chromatography over silica gel using EtOAc/MeOH (95:5) to afford the corresponding sulfoxonium ylides. (b) General procedures for naphthol synthesis A pressure tube was charged with [Cp*Rh(MeCN) 3](SbF 6) 2 (10.0 mg, 6 mol %), Zn(OAc) 2 (3.7 mg, 10 mol %), sulfoxonium ylides (1, 0.2 mmol), alkyne (2, 0.22 mmol) and DCE (4 ml). The reaction mixture was stirred under N 2 condition at 80 C for 16 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using PE/EA to afford the product. S2

3 III. Characterization Data 3,4-diphenylnaphthalen-1-ol 2 White solid, 55.7 mg, yield: 94% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.29 (brs, 1H), 8.36 (d, J = 7.7 Hz, 1H), 7.53 (d, J = 8.6 Hz, 1H), (m, 1H), (m, 1H), (m, 3H), (m, 7H), 7.03 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 152.4, 142.4, 139.4, 138.9, 134.0, 131.9, 129.9, 129.2, 127.8, 127.5, 126.5, 126.4, 126.2, 126.2, 124.5, 124.3, 122.1, methyl-3,4-diphenylnaphthalen-1-ol White solid, 57.1 mg, yield: 92% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.18 (brs, 1H), 8.26 (d, J = 9.1 Hz, 1H), (m, 5H), (m, 7H), 6.96 (s, 1H), 2.34 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 152.4, 142.5, 139.6, 139.0, 136.0, 134.3, 131.9, 129.9, 128.7, 127.7, 127.5, 126.6, 126.3, 126.1, 125.3, 122.5, 122.1, 109.6, HRMS (ESI): calculated for C 23H 17O , found (tert-butyl)-3,4-diphenylnaphthalen-1-ol White solid, 67.3 mg, yield: 95% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.16 (brs, 1H), 8.30 (d, J = 8.8 Hz, 1H), (m, 2H), (m, 3H), (m, 7H), 6.98 (s, 1H), 1.25 (s, 9H). 13 C NMR (100 MHz, acetone-d 6) δ 152.3, 148.9, 142.6, 139.6, 138.9, 134.0, 131.9, 129.9, 129.3, 127.7, 127.5, 126.3, 126.1, 123.3, 122.5, 121.9, 121.4, 109.8, 34.6, HRMS (ESI): calculated for C 26H 23O , found methoxy-3,4-diphenylnaphthalen-1-ol Yellow solid, 61.4 mg, yield: 94% (purified by silica gel chromatography using PE/EA 10:1). 1 H S3

4 NMR (400 MHz, acetone-d 6) δ 9.16 (brs, 1H), 8.27 (d, J = 9.1 Hz, 1H), (m, 3H), (m, 8H), 6.91 (d, J = 2.5 Hz, 1H), 6.88 (s, 1H), 3.65 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 158.4, 152.5, 142.6, 139.7, 139.7, 135.5, 131.8, 129.8, 128.3, 127.8, 127.5, 126.4, 126.1, 123.8, 119.5, 116.3, 108.5, 105.4, HRMS (ESI): calculated for C 23H 17O , found ,4,6-triphenylnaphthalen-1-ol Yellow solid, 70.4 mg, yield: 95% (purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.39 (brs, 1H), 8.46 (d, J = 8.6 Hz, 1H), (m, 2H), 7.56 (d, J = 7.5 Hz, 2H), 7.38 (t, J = 7.5 Hz, 2H), (m, 11H), 7.07 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 152.5, 142.4, 141.2, 139.6, 139.3, 139.0, 134.4, 132.0, 129.9, 129.6, 128.9, 127.8, 127.6, 127.4, 127.1, 126.5, 126.2, 124.2, 124.0, 123.5, 123.0, HRMS (ESI): calculated for C 28H 19O , found fluoro-3,4-diphenylnaphthalen-1-ol White solid, 59.6 mg, yield: 95% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.45 (brs, 1H), 8.41 (dd, J = 9.0, 6.3 Hz, 1H), (m, 4H), (m, 8H), 7.02 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ (d, J C-F = Hz), 152.6, 142.0, 140.5, 139.0, (d, J C-F = 8.8 Hz), 131.7, 129.8, (d, J C-F = 5.2 Hz), 128.0, 127.6, 126.7, 126.4, (d, J C-F = 9.3 Hz), 121.3, (d, J C-F = 25.3 Hz), (d, J C-F = 1.9 Hz), (d, J C-F = 22.3 Hz). HRMS (ESI): calculated for C 22H 14FO , found chloro-3,4-diphenylnaphthalen-1-ol White solid, 58.1 mg, yield: 88% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.54 (brs, 1H), 8.35 (d, J = 8.8 Hz, 1H), (m, 2H), (m, 3H), (m, 7H), 7.05 (s, 1H). 1 H NMR (400 MHz, CDCl 3) δ 8.23 (d, J = 8.9 Hz, 1H), 7.60 (d, J = 1.8 Hz, 1H), 7.41 (dd, J = 8.9, 1.9 Hz, 1H), (m, 3H), (m, 7H), 6.90 (s, 1H), 5.90 (brs, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 152.5, 141.9, 140.6, 138.7, 134.9, 132.3, 131.8, 129.8, 128.5, 128.0, 127.6, 126.8, 126.4, 125.0, 124.9, 124.5, 122.6, HRMS (ESI): calculated for C 22H 14ClO , found S4

5 6-bromo-3,4-diphenylnaphthalen-1-ol White solid, 64.8 mg, yield: 86% (purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.52 (brs, 1H), 8.28 (d, J = 8.9 Hz, 1H), 7.68 (d, J = 1.8 Hz, 1H), 7.59 (dd, J = 8.9, 1.9 Hz, 1H), (m, 3H), (m, 7H), 7.07 (s, 1H). 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, J = 8.9 Hz, 1H), 7.77 (d, J = 1.8 Hz, 1H), 7.55 (dd, J = 8.9, 1.9 Hz, 1H), (m, 3H), (m, 7H), 6.89 (s, 1H), 5.39 (brs, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 152.6, 141.9, 140.5, 138.6, 135.3, 131.8, 129.9, 128.5, 128.2, 128.0, (two signals overlapped), 126.8, 126.4, 124.5, 122.7, 120.8, HRMS (ESI): calculated for C 22H 14BrO , found ,4-diphenyl-6-(trifluoromethyl)naphthalen-1-ol White solid, 69.2 mg, yield: 95% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.70 (br, 1H), 8.56 (d, J = 8.8 Hz, 1H), 7.91 (s, 1H), 7.72 (dd, J = 8.8, 1.6 Hz, 1H), (m, 3H), (m, 8H). 13 C NMR (100 MHz, acetone-d 6) δ 152.5, 141.7, 140.8, 138.4, 132.9, 131.8, 130.1, 129.8, 128.0, (q, J C-F = 31.6 Hz), 127.7, 127.0, 126.5, 125.5, (q, J C-F = Hz), 123.9, (q, J C-F = 4.7 Hz), (q, J C-F = 3.1 Hz), HRMS (ESI): calculated for C 23H 14F 3O , found nitro-3,4-diphenylnaphthalen-1-ol Yellow solid, 25.3 mg, yield: 37% (purified by silica gel chromatography using PE/EA 10:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.86 (br, 1H), (m, 2H), 8.21 (dd, J = 9.2, 2.3 Hz, 1H), (m, 3H), (m, 8H). 13 C NMR (100 MHz, acetone-d 6) δ 152.5, 146.3, 141.5, 141.3, 138.0, 132.9, 131.8, 131.2, 129.8, 128.1, 127.8, 127.2, 126.7, 126.4, 124.4, 122.7, 117.6, HRMS (ESI): calculated for C 22H 14NO , found S5

6 7-methyl-3,4-diphenylnaphthalen-1-ol White solid, 58.1 mg, yield: 94% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.14 (br, 1H), 8.14 (s, 1H), 7.43 (d, J = 8.7 Hz, 1H), (m, 4H), (m, 7H), 7.00 (s, 1H), 2.50 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 152.0, 142.5, 139.6, , 134.1, 132.3, 131.8, 129.9, 129.1, 128.6, 127.7, 127.5, 126.3, 126.2, 126.0, 124.4, 121.1, 110.3, HRMS (ESI): calculated for C 23H 17O , found bromo-3,4-diphenylnaphthalen-1-ol White solid, 73.6 mg, yield: 98% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.59 (brs, 1H), 8.49 (d, J = 1.8 Hz, 1H), 7.53 (dd, J = 9.1, 2.0 Hz, 1H), 7.45 (d, J = 9.1 Hz, 1H), (m, 3H), (m, 7H), 7.08 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 151.5, 141.9, 139.7, 138.8, 132.5, 131.8, 129.8, 129.6, 129.4, 128.6, 127.9, 127.6, 126.7, 126.4, 125.4, 124.3, 118.4, HRMS (ESI): calculated for C 22H 14BrO , found chloro-3,4-diphenylnaphthalen-1-ol Yellow solid, 62.3 mg, yield: 94% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.20 (brs, 1H), 7.52 (dd, J = 7.4, 1.1 Hz, 1H), 7.46 (dd, J = 8.6, 1.1 Hz, 1H), (m, 4H), (m, 7H), 7.10 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 153.0, 141.5, 140.0, 139.4, 136.7, 131.8, 129.9, 129.7, 129.6, 127.9, 127.9, 127.6, 126.7, 126.4, 126.2, 126.0, 120.8, HRMS (ESI): calculated for C 22H 14ClO , found fluoro-3,4-diphenylnaphthalen-1-ol White solid, 60.5 mg, yield: 96% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR S6

7 (400 MHz, acetone-d 6) δ 8.97 (brs, 1H), (m, 5H), (m, 8H), 7.05 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ (d, J C-F = Hz), (d, J C-F = 3.0 Hz), 141.7, 140.4, 139.3, (d, J C-F = 3.5 Hz), 131.7, 129.7, (d, J C-F = 3.0 Hz), 127.9, 127.6, 126.7, 126.4, (d, J C-F =9.2 Hz), (d, J C-F = 4.3 Hz), (d, J C-F = 10.2 Hz), (d, J C-F = 1.8 Hz), (d, J C-F = 21.8 Hz). HRMS (ESI): calculated for C 22H 14FO , found methyl-3,4-diphenylnaphthalen-1-ol Yellow solid, 21.3 mg, yield: 34% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.07 (brs, 1H), (m, 1H), (m, 3H), (m, 2H), (m, 7H), 6.99 (s, 1H), 3.01 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 154.8, 142.2, 140.2, 138.7, 135.7, 135.3, 131.9, 129.8, 129.7, 127.7, (two overlapping signals), , 126.1, 125.9, 124.8, 123.5, 111.6, HRMS (ESI): calculated for C 23H 17O , found ,5-diphenylbenzo[b]thiophen-7-ol White solid, 20.2 mg, yield: 33% (purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.43 (brs, 1H), 7.61 (d, J = 5.4 Hz, 1H), (m, 3H), (m, 7H), 7.09 (d, J = 5.4 Hz, 1H), 6.93 (s, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 151.1, 141.8, 141.7, 139.9, 138.6, 131.0, 130.1, 127.8, 127.7, 127.6, 127.1, 126.7, 126.4, 126.2, 124.3, HRMS (ESI): calculated for C 20H 13OS , found ,4-di-p-tolylnaphthalen-1-ol White solid, 60.3 mg, yield: 93% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.18 (brs, 1H), 8.34 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 9H), 2.31 (s, 3H), 2.22 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 152.2, 139.6, 138.8, 136.5, 135.7, 135.5, 134.3, 131.7, 129.8, 129.1, 128.5, 128.3, 126.4, 126.3, 124.4, 124.2, 122.0, 110.4, 20.4, HRMS (ESI): calculated for C 24H 19O , found S7

8 3,4-bis(4-(tert-butyl)phenyl)naphthalen-1-ol White solid, 80.2 mg, yield: 98% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.21 (brs, 1H), 8.34 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 8.4 Hz, 1H), (m, 2H), 7.32 (d, J = 8.3 Hz, 2H), 7.18 (d, J = 8.4 Hz, 2H), (m, 5H), 1.31 (s, 9H), 1.24 (s, 9H). 13 C NMR (100 MHz, acetone-d 6) δ 152.3, 149.0, 148.6, 139.5, 138.9, 136.5, 134.1, 131.6, 129.6, 129.2, 126.4, 126.3, 124.5, 124.3, 124.2, 122.0, 110.3, 34.1, 34.0, 30.8, HRMS (ESI): calculated for C 30H 31O , found ,4-bis(4-methoxyphenyl)naphthalen-1-ol Yellow solid, 64.1 mg, yield: 90% (purified by silica gel chromatography using PE/EA 10:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.16 (brs, 1H), 8.33 (d, J = 8.1 Hz, 1H), 7.55 (d, J = 8.3 Hz, 1H), (m, 2H), (m, 5H), 6.85 (d, J = 8.4 Hz, 2H), 6.73 (d, J = 8.5 Hz, 2H), 3.77 (s, 3H), 3.71 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 158.3, 158.2, 152.2, 138.7, 134.8, 134.5, 132.8, 131.6, 131.0, 128.8, 126.4, 126.3, 124.3, 124.2, 122.0, 113.2, 113.0, 110.5, 54.5, HRMS (ESI): calculated for C 24H 19O , found ,4-bis(4-fluorophenyl)naphthalen-1-ol White solid, 62.0 mg, yield: 93% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.36 (brs, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 4H), (m, 2H), 7.01 (s, 1H), (m, 2H). 13 C NMR (100 MHz, S8

9 acetone-d 6) δ (d, J C-F = Hz), 161.4(d, J C-F = Hz), 152.6, 138.5, , 138.2, 135.4, 135.4, 134.0, (d, J C-F = 8.0 Hz), (d, J C-F = 8.0 Hz), 128.2, 126.8, 126.0, 124.7, 124.3, 122.2, (d, J C-F = 21.3 Hz), (d, J C-F = 21.4 Hz), HRMS (ESI): calculated for C 22H 13F 2O , found ,4-bis(4-bromophenyl)naphthalen-1-ol Yellow solid, 82.8 mg, yield: 91% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.39 (brs, 1H), 8.36 (d, J = 8.1 Hz, 1H), (m, 5H), 7.40 (d, J = 8.2 Hz, 2H), (m, 4H), 6.99 (s, 1H). 1 H NMR (400 MHz, CDCl 3) δ 8.31 (d, J = 8.2 Hz, 1H), 7.57 (d, J = 8.4 Hz, 1H), 7.51 (t, J = 7.3 Hz, 1H), (m, 3H), 7.31 (d, J = 8.3 Hz, 2H), 7.02 (d, J = 8.2 Hz, 2H), 6.96 (d, J = 8.3 Hz, 2H), 6.88 (s, 1H), 6.60 (brs, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 152.9, 141.3, 138.4, 137.7, 133.8, 133.7, 131.9, 131.0, 130.8, 127.8, 127.0, 125.9, 124.9, 124.4, 122.2, 120.4, 120.2, HRMS (ESI): calculated for C 22H 13Br 2O , found ,4-bis(4-(trifluoromethyl)phenyl)naphthalen-1-ol Yellow solid, 76.0 mg, yield: 88% (purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.53 (brs, 1H), 8.40 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 8.0 Hz, 2H), (m, 3H), (m, 2H), (m, 4H), 7.05 (s, 1H). 1 H NMR (400 MHz, CDCl 3) δ 8.32 (d, J = 8.3 Hz, 1H), (m, 4H), (m, 3H), 7.30 (d, J = 8.0 Hz, 2H), 7.22 (d, J = 8.1 Hz, 2H), 6.90 (s, 1H), 5.56 (brs, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 153.2, 146.0, 143.4, 137.7, 133.5, 132.6, 130.6, 128.5, 128.2, 127.9, 127.3, 125.8, 125.2, (q, J C-F = 3.8 Hz), (q, J C-F = 3.7 Hz), 124.6, (q, J C-F = Hz), (q, J C-F = Hz), 122.3, HRMS (ESI): calculated for C 24H 13F 6O , found S9

10 3,4-bis(3-fluorophenyl)naphthalen-1-ol Yellow solid, 60.6 mg, yield: 91% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.41 (brs, 1H), 8.38 (d, J = 8.4 Hz, 1H), (m, 3H), (m, 1H), (m, 1H), (m, 4H), (m, 3H). 13 C NMR (100 MHz, acetone-d 6) δ (d, J C-F = Hz), (d, J C-F = Hz), 152.9, (d, J C-F = 7.9 Hz), (d, J C-F = 7.9 Hz), 137.7, 137.7, 133.6, (d, J C-F = 8.6 Hz), (d, J C-F = 8.5 Hz), (d, J C-F = 2.8 Hz), 127.0, 126.0, (d, J C-F = 2.8 Hz), 125.0, 124.4, 122.2, (d, J C-F = 21.0 Hz), (d, J C-F = 21.8 Hz), (d, J C-F = 21.0 Hz), (d, J C-F = 21.1 Hz), HRMS (ESI): calculated for C 22H 13F 2O , found ,4-di-m-tolylnaphthalen-1-ol White solid, 62.3 mg, yield: 96% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.21 (brs, 1H), 8.34 (d, J = 8.4 Hz, 1H), 7.53 (d, J = 8.5 Hz, 1H), (m, 1H), (m, 1H), 7.17 (t, J = 7.5 Hz, 1H), (m, 5H), (m, 3H), 2.26 (s, 3H), 2.19 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 152.3, 142.3, 139.4, 138.8, 137.0, 136.8, 134.1, 132.5, 130.7, 129.3, 128.9, 127.6, 127.4, 127.0, 127.0, 126.8, 126.4, 126.4, 124.4, 124.2, 122.0, 110.3, 20.6, HRMS (ESI): calculated for C 24H 19O , found ,4-bis(2-fluorophenyl)naphthalen-1-ol White solid, 65.8 mg, yield: 99% (purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.42 (brs, 1H), 8.38 (d, J = 8.2 Hz, 1H), (m, 3H), (m, 1H), (m, 3H), (m, 5H). 13 C NMR (100 MHz, acetone-d 6) δ (d, J C-F = Hz), (d, J C-F = Hz), 152.9, 134.1, 133.7, (d, J C-F = 3.2 Hz), (d, J C-F = 3.1 S10

11 Hz), (d, J C-F = 24.9 Hz), 129.2(d, J C-F = 25.1 Hz), 127.0, 126.5, 126.3, 125.7, 125.0, 124.6, 124.1, (d, J C-F = 3.5 Hz), (d, J C-F = 3.6 Hz), 122.3, (d, J C-F = 22.4 Hz), (d, J C-F = 22.6 Hz), HRMS (ESI): calculated for C 22H 13F 2O , found ,4-di(thiophen-2-yl)naphthalen-1-ol Yellow solid, 55.2 mg, yield: 89% (purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.47 (brs, 1H), (m, 1H), (m, 2H), (m, 2H), 7.36 (d, J = 4.6 Hz, 1H), 7.28 (s, 1H), (m, 1H), (m, 2H), (m, 1H). 13 C NMR (100 MHz, acetone-d 6) δ 153.6, 143.2, 139.7, 135.6, 133.4, 130.0, 127.2, 127.1, 127.0, 126.9, 126.7, 126.6, 126.3, 125.0, 124.3, 122.0, 120.3, HRMS (ESI): calculated for C 18H 11OS , found methyl-4-hydroxy-2-phenyl-1-naphthoate Yellow solid, 21.0 mg, yield: 38% (purified by silica gel chromatography using PE/EA 20:1 to 10:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.64 (brs, 1H), 8.34 (dd, J = 8.3, 0.7 Hz, 1H), 7.97 (d, J = 8.3 Hz, 1H), (m, 1H), (m, 1H), (m, 4H), (m, 1H), 7.00 (s, 1H), 3.61 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 169.5, 154.4, 141.5, 139.5, 131.8, 128.4, 128.2, 127.8, 127.5, 125.2, 124.9, 123.7, 122.3, 121.9, 109.4, HRMS (ESI): calculated for C 18H 13O , found methyl-4-hydroxy-1-phenyl-2-naphthoate White solid, 15.1 mg, yield: 27% (purified by silica gel chromatography using PE/EA 20:1 to 10:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.43 (brs, 1H), 8.35 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 5H), 7.32 (s, 1H), (m, 2H), 3.50 (s, 3H). 1 H NMR (400 MHz, CDCl 3) δ 8.29 (d, J = 7.9 Hz, 1H), (m, 2H), (m, 5H), (m, 3H), 6.26 (brs, 1H), 3.58 (s, S11

12 3H). 13 C NMR (100 MHz, acetone-d 6) δ 168.2, 152.5, 139.3, 133.7, 132.2, 130.2, 129.1, 127.8, 127.1, 127.0, 126.9, 126.3, 126.2, 122.1, 107.1, 100.0, HRMS (ESI): calculated for C 18H 13O , found methyl 2-(4-hydroxy-2-phenylnaphthalen-1-yl)benzoate Yellow solid, 62.4 mg, yield: 88%, 6:1 (only the major isomer was shown, purified by silica gel chromatography using PE/EA 20:1). 1 H NMR (400 MHz, acetone-d 6) δ 9.19 (brs, 1H), 8.34 (d, J = 8.3 Hz, 1H), 7.85 (d, J = 7.7 Hz, 1H), (m, 2H), (m, 2H), 7.29 (d, J = 8.4 Hz, 1H), (m, 7H), 7.01 (s, 1H), 3.41 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 167.0, 152.3, 142.4, 140.5, 138.1, (two signals overlapped), 132.9, 131.3, 129.6, 129.6, 128.7, 127.5, 127.0, 126.4, 126.3, 125.6, 124.3, 124.1, 122.1, 110.2, HRMS (ESI): calculated for C 24H 17O , found methyl-3-phenylnaphthalen-1-ol Colorless oil, 39.0 mg, yield: 83%, >20:1 (only the major isomer was shown, purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 8.96 (brs, 1H), 8.32 (dd, J = 8.3, 0.8 Hz, 1H), 8.04 (d, J = 8.4 Hz, 1H), (m, 1H), (m, 3H), (m, 3H), 6.86 (s, 1H), 2.46 (s, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 151.0, 142.9, 139.2, 134.1, 129.5, 128.1, 126.7, 126.5, 124.6, 124.4, 124.3, 122.4, 121.3, 110.2, HRMS (ESI): calculated for C 17H 13O , found ethyl-3-phenylnaphthalen-1-ol Colorless oil, 40.0 mg, yield: 80%, 17:1 (only the major isomer was shown, purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 8.96 (brs, 1H), 8.33 (dd, J = 8.3, 0.9 Hz, 1H), 8.08 (d, J = 8.5 Hz, 1H), (m, 1H), (m, 3H), (m, 3H), 6.79 (s, 1H), 2.91 (q, J = 7.5 Hz, 2H), 1.16 (t, J = 7.5 Hz, 3H). 13 C NMR (100 MHz, acetone-d 6) δ S12

13 150.8, 143.1, 139.1, 133.0, 129.0, 128.1, 128.0, 126.8, 126.5, 125.0, 124.3, 124.2, 122.7, 110.3, 21.6, HRMS (ESI): calculated for C 18H 15O , found phenyl-4-propylnaphthalen-1-ol Colorless oil, 44.7 mg, yield: 85%, 17:1 (only the major isomer was shown, purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 8.99 (brs, 1H), 8.33 (dd, J = 8.3, 0.9 Hz, 1H), 8.07 (d, J = 8.5 Hz, 1H), (m, 1H), (m, 3H), (m, 3H), 6.80 (s, 1H), (m, 2H), (m, 2H), 0.84 (t, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 150.9, 143.2, 139.4, 133.3, 129.2, 128.0, 126.7, 126.7, 126.5, 124.9, 124.5, 124.2, 122.6, 110.3, 30.8, 24.7, HRMS (ESI): calculated for C 19H 17O , found butyl-3-phenylnaphthalen-1-ol Yellow oil, 44.4 mg, yield: 80%, 14:1 (only the major isomer was shown, purified by silica gel chromatography using PE/EA 30:1). 1 H NMR (400 MHz, acetone-d 6) δ 8.95 (brs, 1H), 8.33 (dd, J = 8.3, 0.9 Hz, 1H), 8.08 (d, J = 8.5 Hz, 1H), (m, 1H), (m, 3H), (m, 3H), 6.80 (s, 1H), (m, 2H), (m, 2H), (m, 2H), 0.79 (t, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, acetone-d 6) δ 150.8, 143.3, 139.3, 133.3, 129.2, 128.0, 126.8, 126.7, 126.4, 124.9, 124.4, 124.2, 122.6, 110.3, 33.7, 28.2, 22.7, HRMS (ESI): calculated for C 20H 19O , found IV. Gram-Scale Preparation and Transformations (a) Gram-Scale Preparation of 3aa A pressure tube was charged with [Cp*Rh(MeCN) 3](SbF 6) 2 (255 mg, 6 mol %), Zn(OAc) 2 (94 mg, 10 mol %), sulfoxonium ylides (1.0 g, 5.1 mmol), alkyne (1.1 equiv). and DCE (80 ml). The reaction mixture was stirred under N 2 condition at 80 C for 24 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using PE/EA to afford S13

14 product 3aa as a white solid (1.38 g, 91%). (b) Transformations of 3aa Naphthol 3aa (296.4 mg, 1.0 mmol) was dissolved in DCM (5.0 ml) and then cooled to -78 o C. Triethylamine (TEA, μl, 1.5 mmol) was added, followed by addition of trifluoromethanesulfonic anhydride (Tf 2O, μl, 1.5 mmol) within 5 minutes via a syringe. The resulting solution was gradually warmed to room temperature and stirred for 2 h until 3aa had been completely consumed as determined by TLC. The solvent was then removed under reduced pressure to get the crude product, which was purified by flash column chromatography on silica gel, eluted by ethyl acetate/hexane = 1:100 to afford the pure product 4a as a yellow solid (404.0 mg, 94% yield). 2 4a (42.8 mg, 0.1 mmol), phenylacetylene (33.0 μl, 0.3 mmol), bis(triphenylphosphine)palladium(ii) dichloride (Pd(PPh 3) 2Cl 2, 7.0 mg, 0.01 mmol), copper(i) bromide (CuBr, 0.7 mg, mmol), diisopropylethylamine (DIPEA, 52.0 μl, 0.3 mmol), and DMF (1.0 ml) were added to a pressure tube. The reaction mixture was heated to 80 C under N 2 condition for 5 h until 4a had been completely consumed as determined by TLC. Work-up: the reaction mixture was cooled down to room temperature and then diluted with ethyl acetate (50 ml). The organic phase was washed with brine (4*10 ml) and dried with MgSO 4. The solvent was removed under reduced pressure to get the crude product, which was purified by flash column chromatography on silica gel, eluted by PE to afford the pure product as a white solid (90% yield). 3 1 H NMR (400 MHz, CDCl 3) δ 8.56 (d, J = 8.3 Hz, 1H), 7.92 (s, 1H), (m, 3H), 7.62 (t, J = 7.3 Hz, 1H), (m, 4H), (m, 3H), (m, 7H). 13 C NMR (100 MHz, CDCl 3) δ 141.2, 138.6, 138.5, 138.1, 132.7, 132.6, 132.5, 131.7, 131.3, 130.0, 128.4, 128.4, 127.8, 127.7, 127.3, 126.9, 126.7, 126.5, 126.4, 126.2, 123.4, 120.5, 94.4, a (42.8 mg, 0.1 mmol), ethyl acrylate (106.4 μl, 1.0 mmol), palladium(ii) aceate (Pd(OAc) 2, 4.4 mg, 0.02 mmol), triphenylphosphine (PPh 3, 15.7 mg, 0.06 mmol), potassium carbonate (K 2CO 3, 27.6 S14

15 mg, 0.2 mmol), and toluene (1.0 ml) were added to a pressure tube. The reaction mixture was heated at 110 C under N 2 condition for 6 h until 4a had been completely consumed as determined by TLC. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure to get the crude product, which was purified by flash column chromatography on silica gel, eluted by PE/EA = 40:1 to afford the pure product as a white solid (85% yield). 3 1 H NMR (400 MHz, CDCl 3) δ 8.62 (d, J = 15.8 Hz, 1H), 8.29 (d, J = 8.4 Hz, 1H), 7.87 (s, 1H), 7.73 (d, J = 8.0 Hz, 1H), (m, 1H), (m, 1H), (m, 3H), m, 7H), 6.61 (d, J = 15.7 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3) δ 166.9, 141.5, 141.3, 140.0, 138.6, 138.3, 133.0, 131.3, 131.2, 130.7, 130.0, 127.9, 127.7, 127.7, 127.4, 127.0, 126.5, 126.5, 126.5, 123.3, 121.2, 60.6, HRMS (ESI): calculated for C 27H 23O , found V. Mechanistic Studies A pressure tube was charged with Zn(OAc) 2 (1.8 mg, 10 mol %), sulfoxonium ylides (19.6 mg, 0.1 mmol), CD 3OD (36 mg, 10 eq), and DCE (2 ml). The reaction mixture was stirred under N 2 condition at 80 C for 12 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using EA to afford compound, which was characterized by 1 H NMR spectroscopy. 1 H NMR analysis of 1a revealed no deuteration at the 2-position of phenyl ring or the α-position of the carbonyl. S15

16 A pressure tube was charged with [Cp*Rh(MeCN) 3](SbF 6) 2 (5 mg, 6 mol %), Zn(OAc) 2 (1.8 mg, 10 mol %), sulfoxonium ylides (19.6 mg, 0.1 mmol), CD 3OD (36 mg, 10 eq) and DCE (2 ml). The reaction mixture was stirred under N 2 condition at 80 C for 1 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using EA to afford compound, which was characterized by 1 H NMR spectroscopy. 1 H NMR analysis of 1a revealed 7% deuteration at the 2-position of phenyl ring and 10% deuteration the α-position of the carbonyl. Two pressure tubes were charged with [Cp*Rh(MeCN) 3](SbF 6) 2 (10.0 mg, 6 mol %), Zn(OAc) 2 (3.7 mg, 10 mol %), sulfoxonium ylides (1a or 1a-d5, 0.2 mmol), alkyne (2g, 0.22 mmol) and DCE (4 ml). The reaction mixture was stirred under N 2 condition at 80 C for 15 min. After that, the reaction was S16

17 cooled to 0 o C rapidly and was quenched with pentane. Then the solvent was removed under vacuum and the residue was purified by silica gel chromatography using PE/EA to afford compound 3ag and 3ag-d4 (20% yield in total). The KIE value was determined to be k H/k D = 1.3 on the basis of 1 H NMR analysis. VI. References (1) (a) Vaitla, J.; Bayer, A.; Hopmann, K. H. Angew. Chem., Int. Ed. 2017, 56, 4277; (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353; (c) Wang, D.; Schwinden, M. D.; Radesca, L.; Patel, B.; Kronenthal, D.; Huang, M. H.; Nugent, W. A. J. Org. Chem. 2004, 69, 1629; (d) Dias, R. M. P.; Burtoloso, A. C. B. Org. Lett. 2016, 18, 3034; (d) Phelps, A. M.; Chan, V. S.; Napolitano, J. G.; Krabbe, S. W.; Schomaker, J. M.; Shekhar, S. J. Org. Chem. 2016, 81, (2) Chai, G.; Lu, Z.; Fu, C.; Ma, S. Chem. Eur. J. 2009, 15, (3) Peng, S.; Wang, L.; Wang, J. Chem. Eur. J. 2013, 19, S17

18 VII. NMR Spectra of Products S18

19 S19

20 S20

21 S21

22 S22

23 S23

24 S24 H2O

25 S25

26 S26

27 S27

28 S28

29 S29

30 S30

31 S31

32 S32

33 S33

34 H 2O CD 3COCD 3 S34

35 S35

36 S36

37 S37

38 S38 H 2O

39 H 2O CD 3COCD 3 S39

40 H 2O CD 3COCD 3 S40

41 S41

42 S42

43 S43

44 S44

45 S45

46 S46 H 2O CD 3COCD 3

47 H 2O CD 3COCD 3 S47

48 S48

49 S49

50 S50

51 S51

52 S52

53 S53

54 S54

55 S55

56 S56

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