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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. 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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