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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H Bond Acylation of Azoxybenzenes with Alcohols Lekai Hou, b Xiangxiang Chen, b Shuang Li, Suxian Cai, Yanxia Zhao, Meng Sun a * and Xiao-Juan Yang a Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi an , P. R. China b These two authors contributed equally to this work. * To whom correspondence should be addressed. sunmeng@nwu.edu.cn Contents: 1. General methods and experimental procedures 2. Characterization of the Products 3. NMR Chart 4. In-situ NMR Chart 5. Crystal structure 6. References 1. General methods. All reactions involving air- and moisture-sensitive reagents were carried out under a nitrogen atmosphere. Toluene, DMF, 1, 2-dichloroethane, DMS, 1, 4- dioxane and CH 3 CN were distilled from appropriate drying agents prior to use. All chemicals were purchased from Aldrich and used without further purification. Thin-layer chromatography (TLC) was performed using 60 mesh silica gel plates visualized with short-wavelength UV light (254 nm). Silica gel 60 (230~400 mesh) was used for column chromatography. 1 H NMR and 13 C NMR spectra were recorded on a Bruker S1
2 INVA-400. NMR Spectrums were recorded on a 400 instrument (400 MHz for 1 H and 100 MHz for 13 C). Chemical shifts (δ) were measured in ppm relative to TMS δ = 0 for 1 H, or to chloroform δ = 77.0 for 13 C as internal standard. Data are reported as follows: Chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet), Coupling constants, J, are reported in hertz. Mass data were measured with Thermo Scientific DSQ II mass spectrometer. Azoxybenzenes were prepared from arylamines, according to the literature 1. General Catalytic Procedure for rtho-acylation of Azoxybenzenes with Alcohol Derivatives. Pd(TFA) 2 (6.6 mg, 0.02 mmol, 10 mol %), azoxybenzene (39.6 mg, 0.2 mmol, 1.0 equiv), benzyl alcohol (64.8 mg, 0.6 mmol, 3.0 equiv), TBHP (196µl, 70%, 1.4 mmol, 7.0 equiv) and DCE (1.0 ml) were added in a 10 ml sealed tube with a Teflon-lined cap. The vessel was heated in an oil bath at 100 o C for 20 h followed by cooling. The contents were subjected to flash chromatography (eluent: petroleum ether/etac = 20:1) to give the corresponding product (73%) as a pale yellow oil. The purified material was dried under an oil-pump vacuum.. 2. Characterization of the Products 3aa: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), 7.68 (dd, J = 4.0 Hz, J = 4.0 Hz, 4 H), (m, 2 H), (m, 5 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 14 N 2 2 : , Found: ab: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: 8.24 (s, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 8.0Hz, 4 H), 7.51 (s, 1 H), (d, J = 8.0Hz, 3 H), (d, J = 4.0 Hz, S2
3 2 H), 2.34 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 20 H 16 N 2 2 : , Found: ac: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 8.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 4.0 Hz, 2 H), 7.60 (s, 1 H), (d, J = 8.0 Hz, 2 H), (m, 5 H), 2.29 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 20 H 16 N 2 2 : , Found: ad: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), 7.63 (s, 3 H), (d, J = 8.0 Hz, 2 H), (m, 5 H), (m, 2 H), 2.53 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 20 H 16 N 2 2 : , Found: ae: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 8.0 Hz, 1 H), (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 1 H), (d, J = 8.0 Hz, 1 H), (m, 3 H), (m, 2 H), (t, J = 8.0 Hz, 1 H), (d, J = 4.0 Hz, 2 H), (t, J = 8.0 Hz, 1 H),7.12 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 23 H 16 N 2 2 : , Found: S3
4 Me 3af: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 4 H), (d, J = 4.0 Hz, 2 H), 7.49 (s, 1 H), (d, J = 8.0 Hz, 3 H), (d, J = 8.0 Hz, 2 H), 3.79 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 20 H 16 N 2 3 : , Found: Me Me 3ag: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (t, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (m, 2 H), 7.53 (s, 1 H), (d, J = 8.0 Hz, 3 H), 6.88 (s, 2 H), 6.55 (s, 1 H), 3.72 (s, 6 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 21 H 18 N 2 4 : , Found: F 3ah: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (m, 4 H), (d, J = 8.0 Hz, 2 H), (d, J = 4.0 Hz, 1 H), (d, J = 4.0 Hz, 3 H), (t, J = 8.0 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , (d, J = Hz), , , , (d, J = 3.0 Hz), , , , , , , , , (d, J = 22.0 Hz). HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 13 FN 2 2 : , Found: S4
5 Cl 3ai: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (m, 1 H), (d, J = 4.0 Hz, 2 H), (m, 4 H), (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 5 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 13 ClN 2 2 : , Found: Br 3aj: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (m, 4 H), (d, J = 8.0 Hz, 3 H), (m, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 13 BrN 2 2 : , Found: CN 3ak: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (d, J = 4.0 Hz, 2 H), (m, 4 H), (d, J = 8.0 Hz, 2 H), 7.55 (s, 1 H), 7.33 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 20 H 13 N 3 2 : , Found: S5
6 N 2 3al: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 8.0 Hz, 2 H), (m, 4 H), 7.56 (s, 1 H), 7.32 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 13 N 3 4 : , Found: am: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 4.0 Hz, 3 H), (d, J = 4.0 Hz, 2 H), (t, J = 8.0 Hz, 2 H), (d, J = 4.0 Hz, 2 H), (t, J = 8.0 Hz, 2 H), (m, 2 H), (t, J = 8.0 Hz, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , 44.88, 17.68, HRMS (ESI) ([M+Na] + ) Calcd. for C 16 H 16 N 2 2 : , Found: ba: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 8.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 8.0 Hz, 2 H), (m, 2 H), (t, J = 8.0 Hz, 2 H), 7.28 (s, 1 H), (d, J = 8.0 Hz, 2 H) (s, 3 H), 2.30 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , 21.47, HRMS (ESI) ([M+Na] + ) Calcd. for C 21 H 18 N 2 2 : , Found: S6
7 3ca: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: 8.00 (s, 1 H), (m, 2 H), (m, 5 H), (m, 2 H), (t, J = 8.0 Hz, 1 H), (d, J = 4.0 Hz, 1 H), 2.53 (s, 3 H), 2.28 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , , , 21.32, HRMS (ESI) ([M+Na] + ) Calcd. for C 21 H 18 N 2 2 : , Found: da: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (m, 2 H), (d, J = 8.0 Hz, 1 H), (m, 6 H), (m, 2 H), (m, 1 H), 2.53 (s, 3 H), 2.21 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , , , 18.28, HRMS (ESI) ([M+Na] + ) Calcd. for C 21 H 18 N 2 2 : , Found: Me Me 3ea: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 12.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 4.0 Hz, 2 H), (d, J = 8.0 Hz, 1 H), (t, J = 8.0 Hz, 2 H), (d, J = 12.0 Hz, 1 H), 6.94 (s, 1 H), (d, J = 8.0 Hz, 2 H), 3.89 (s, 3 H), 3.79 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , , , 55.90, HRMS (ESI) ([M+Na] + ) Calcd. for C 21 H 18 N 2 4 : , Found: S7
8 F F 3fa: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (t, J = 4.0 Hz, 1 H), (m, 4 H), (m, 1 H), (m, 3 H), (d, J = 8.0 Hz, 1 H), (t, J = 8.0 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , (d, J = Hz), (d, J = Hz), , , (d, J = 7.0 Hz), , , (d, J = 9.0 Hz), (d, J = 8.0 Hz), (d, J = 9.0 Hz), (d, J = 22.0 Hz), (d, J = 24.0 Hz), (d, J = 23.0 Hz). HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 12 F 2 N 2 2 : , Found: Cl Cl 3ga: Pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ: (d, J = 8.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (d, J = 8.0 Hz, 2 H), (d, J = 8.0 Hz, 1 H), (d, J = 8.0 Hz, 2 H), (m, 2 H), (d, J = 8.0 Hz, 2 H). 13 C NMR (100 MHz, CDCl 3 ) δ: , , , , , , , , , , , , , HRMS (ESI) ([M+Na] + ) Calcd. for C 19 H 12 Cl 2 N 2 2 : , Found: S8
9 3. NMR Charts S9
10 S10
11 S11
12 S12
13 S13
14 S14
15 S15
16 S16
17 S17
18 S18
19 Me S19
20 Me S20
21 Me Me S21
22 Me Me S22
23 F S23
24 F S24
25 Cl S25
26 Cl S26
27 Br S27
28 Br S28
29 CN S29
30 CN S30
31 N 2 S31
32 N 2 S32
33 S33
34 S34
35 S35
36 S36
37 S37
38 S38
39 S39
40 S40
41 Me Me S41
42 Me Me S42
43 F F S43
44 F F S44
45 Cl Cl S45
46 Cl Cl S46
47 4. In-situ NMR Chart. Me Me S47
48 Me + Me Me Me In CDCl 3, 1 h, 60 o C Pd TFA I S48
49 Me + Me Me Me In CDCl 3, 24 h, 60 o C Pd TFA I S49
50 Me + Me Me Me In CDCl 3, 72 h, 60 o C Pd TFA I S50
51 5. Crystal structure. X-ray single-crystal for acylated azoxybenzene 3ai (CCDC ) Table 1. Crystal and Refinement Data for 3ai compound 3ai empirical formula C 19 H 13 ClN 2 2 Fw crystal system space group Monoclinic P2(1)/n a /Å 6.021(2) b /Å (6) c /Å (6) α / 90 β / (4) γ / 90 V /Å (10) Z 4 D calc /g cm F (000) 696 µ /mm θ range reflns collected 2812 independent reflns 2045 observed reflns [I > 2σ(I)] 2812 R(int) R 1 ; wr 2 [I > 2σ(I)] , R 1 ; wr 2 (all data) , GF (F 2 ) S51
52 6. References [1] G. Christin, P. Beate, I. Elisabeth, R.-B. Karola, Synthesis, 2008, 2008, S52
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216.29 185.02 164.20 148.97 128.19 87.70 79.67 77.30 77.04 76.79 74.66 26.23 2.02 2.03 2.01 3.05 7.26 6.92 6.90 6.25 6.23 5.61 5.60 5.58 5.25 5.24 1.58 Supplementary Figure 1. 1 H and 13 C NMR spectra
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