Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes

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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes Lei Kang, a Feng Zhang, b Lin-Ting Ding a and Luo Yang*, a a Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, College of Chemistry, Xiangtan University, Hunan, , China. yangluo@xtu.edu.cn; Fax: ; Tel: b College of Science, Hunan Agricultural University, Hunan , China. zhangf@iccas.ac.cn; Tel: Table of Contents 1. General information...s1 2. General experimental procedures...s2 3. Condition optimization...s2 4. Spectra data of products 3a-3t...S Copies of 1H and 13C NMR spectra of products 3a-3t...S General information Thin-layer chromatography (TLC) was performed using E. Merck Silica Gel 60 F254 precoated plates (0.25 mm). The developed chromatography was analyzed by UV lamp (254 nm). Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 spectrometer at ambient temperature. Chemical shifts for 1 H NMR spectra are reported in parts per million (ppm) from tetramethylsilane with the solvent resonance as the internal standard (chloroform: δ 7.26 ppm). Chemical shifts for 13 C NMR spectra are reported in parts per million (ppm) from tetramethylsilane with the solvent as the internal standard (CDCl 3 : δ ppm). Data are reported as following: chemical shift, multiplicity (s = singlet, d = doublet, dd = doublet of doublets, t = triplet, q = quartet, m = multiplet, br = broad signal), coupling constant (Hz), and integration. The (E) to (Z) ratios were determined from the relative integration of the crude 1 H NMR spectra of the resolved olefinic protons. S1

2 2. General experimental procedures A general experimental procedure is described as following: An oven-dried reaction vessel was charged with [Rh(COD)Cl] 2 (0.01 mmol, 2.4 mg, 5 mol%), styrene (0.8 mmol, 83.3 mg), p-cyanobenzaldehyde (1a, 0.2 mmol, 26.2 mg), benzoyl chloride (0.04 mmol, 5.6 mg, 20 mol%), chlorobenzene (0.5 ml), and TBP (2.5 equiv, 0.5 mmol, 94μL) under air. The vessel was sealed and heated at 140 C (oil bath temperature) for 12 h. The resulting mixture was cooled to room temperature, transferred to silica gel column directly and eluted with petroleum ether and ethyl acetate (30:1) to give products 3a (34.0 mg, 83 % yield). 3. Condition optimization Table S1. Optimization of the oxidants Ar CHO 1a, Ar = p NC-C 6 H 4 2a -CO Additive, [O] 140 C, 12 h Ar 3a Entry Oxidant (equiv) Yield (%) [b] 1 TBP 83 2 TBHP < 5 3 K 2 S 2 O 8 < 5 4 BPO (benzoyl peroxide) trace 5 DCP (dicumyl peroxide) < 5 6 H 2 O 2 trace To a solution of 1a (0.2 mmol, 1 equiv.) and 2a (0.8 mmol, 4 equiv.) in chlorobenzene (0.5 ml), oxidant (0.5 mmol, 2.5 equiv.) was added with vigorous stirring. The reaction mixture was stirring at 140 C for 12 h under argon. [b] Isolated yields. S2

3 4. Spectra data of products 3a-3t (3a) 1 NC Yellow solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.64 (d, J = 8.4 Hz, 2H), 7.59 (d, J = 8.4 Hz, 2H), 7.54 (d, J = 7.6 Hz, 2H), 7.41 (t, J = 7.2 Hz, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.22 (d, J = 16.4 Hz, 1H), (d, J = 16 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , ; MS (EI) m/z (%): 205(100)[M] +, 190(26), 177(12), 165(8), 152(6). (3b) 1 H 3 CO 2 C White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.03 (d, J = 7.2 Hz, 2H), (m, 4H), 7.38 (t, J = 6.4 Hz, 2H), 7.31 (d, J = 6.4 Hz, 1H), 7.23 (d, J = 16.8 Hz, 1H), 7.13 (d, J = 16.4 Hz, 1H), 3.93 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , 52.18; MS (EI) m/z (%): 238(90)[M] +, 207(55), 178(100), 165(4), 152(18). (3c) 2 F 3 C White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.60 (s, 4H), 7.54 (d, J = 7.2 Hz,2H), 7.39 (t, J = 6.8 Hz, 2H), 7.31 (t, J = 6.8 Hz, 1H), 7.20 (d, J = 16.4 Hz, 1H), 7.12 (d, J = 16 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , (d, J = 32 Hz), , 1 Sugihara T., Satoh T., Miura M., et al. Advanced Synthesis & Catalysis, 2004, 346(13 15): Chen Z., Luo M., Wen Y., et al. Organic letters, 2014, 16(11): S3

4 128.42, , , , (q, J = 4 Hz), MS (EI) m/z (%): 248(100)[M] +, 233(18), 227(16), 179(76), 152(9). (3d) 2 F White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ (m, 4H), 7.36 (t, J = 7.2 Hz, 2H), 7.27 (t, J = 7.2 Hz, 1H), (m, 4H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = 246 Hz), , (d, J = 3 Hz), , , (d, J = 8 Hz), , , , (d, J = 22 Hz). MS (EI) m/z (%): 198(100)[M] +, 183(42), 177(21), 165(7), 152(5). (3e) 2 Cl White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.51 (d, J = 6.8 Hz, 2H), 7.45 (d, J = 8 Hz, 2H), (m, 5H), 7.07 (dd, J = 16.4 Hz, J = 18.4 Hz, 2H,); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , ,126.66; MS (EI) m/z (%): 214(79)[M] +, 199(6), 178(100), 163(4), 152(13). (3f) 1 Br White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ (m, 4H), (m, 4H), (m, 1H), 7.11 (d, J = 16.4 Hz, 1H),7.04 (d, J = 16.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , ; MS (EI) m/z (%): 258(75)[M-1] +, 243(4), 178(100), S4

5 165(4), 152(10). (3g) 1 White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.52 (d, J = 7.6 Hz, 4H), 7.36 (t, J =8.0 Hz, 4H), (m, 2H), 7.12 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ137.43, , , , MS (EI) m/z (%): 180(100)[M] +, 165(60), 152(16). (3h) 3 NC (E:Z=94:6) Yellow solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.78 (s, 1H), 7.72 (m, 1H), (m, 7H), 7.17 (d, J = 16.4 Hz, 1H), 7.06 (d, J = 16.4 Hz, 1H),; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , MS (EI) m/z (%): 204(100)[M-1] +, 190(35), 176(15), 165(10), 152(9). (3i) 4 F (E:Z=85:15) White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.52 (d, J = 6.8 Hz, 2H), (m, 6H), (m, 2H ), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), (d, J = 7.0 Hz), , , , , , , , , , , , , , , (d, J = 22.0 Hz), (d, J = 21.0 Hz). MS 3 Cui X., Zhou Y., Wang N., et al. Tetrahedron Letters, 2007, 48(1): Zhu X., Liu J., Chen T., et al. ChemInform, 2012, 43(31): no. S5

6 (EI) m/z (%): 198(100)[M] +, 183(50), 178(30), 170(8), 152(5). (3j) 5 Cl White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.51 (m, 3H), 7.37 (m, 3H), (m, 3H), 7.12 (d, J = 16 Hz, 1H), 7.04 (d, J = 16 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , MS (EI) m/z (%): 214(61)[M] +, 199(8), 178(100), 163(5), 152(10). (3k) 6 H 3 CO Yellow oil. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.52 (d, J = 7.2 Hz, 2H), (m, 2H), 7.29 (d, J = 7.2 Hz, 2H), (m, 4H), 6.83 (d, J = 8 Hz, 1H), 3.85 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , MS (EI) m/z (%): 210(100)[M] +, 194(25), 179(40), 165(50), 152(24). (3l) 7 CO 2 CH 3 (E:Z=75:25) Yellow oil. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.52 (d, J = 7.2 Hz, 1H), (m, 9H), 6.65 (d, J = 12.4, 1H), 3.89 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , 5 Zhang Y.-G., Liu X.-L., He Z.-Y., et al. Chemistry-A European Journal, 2014, 20(10): Pavia C., Giacalone F., Bivona L. A., et al. Journal of Molecular Catalysis A: Chemical, 2014, 387: Shahzad S. A., Wirth T., Angewandte Chemie International Edition, 2009, 48(14): S6

7 129.66, , , , , , , MS (EI) m/z (%): 238(92)[M] +, 206(33), 195(13), 178(100), 165(13), 152(20). (3m) 8 H 3 CO OCH 3 H 3 CO Light yellow solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.51 (d, J = 7.2 Hz, 2H), 7.37 (t, J = 7.2 Hz, 2H), 7.27 (t, J = 7.6 Hz, 1H), (dd, J = 17.2 Hz, J = 17.6 Hz, 2H), 6.75 (s, 2H), 3.93 (s, 6H), 3.87 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 56.24, 61.12, , , , , , , , , , MS (EI) m/z (%): 270(100)[M] +, 255(88), 195(18), 180(11), 165(19), 152(20). (3n) 1 White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ (m, 4H), 7.75 (d, J = 8.4 Hz, 1H), 7.57 (d, J = 7.2 Hz, 2H), 7.46 (t, J = 6.4 Hz, 2H), 7.39 (t, J = 6.8 Hz, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , MS (EI) m/z (%): 230(100)[M] +, 215(24), 202(12), 189(5), 152(10). (3o) 9 H 3 CO 2 C F White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 7.03 (d, J = 8.4 Hz, 8 McNulty J., Das P. European Journal of Organic Chemistry, 2009, 2009(24): Palmer B. D., Sutherland H. S., Blaser A., et al. Journal of Medicinal Chemistry, 2015, 58(7): S7

8 2H), 7.55 (d, J = 8.0 Hz, 2H), (dd, J = 5.6 Hz, J = 5.6 Hz, 2H), 7.18 (d, J = 16.4 Hz, 1H), (dd, J = 16.4 Hz, J = 8.4 Hz, 3H), 3.93 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , (d, J = 247 Hz), , (d, J = 3 Hz), , , (d, J = 8 Hz), , , , (d, J = 21 Hz), MS (EI) m/z (%): 256(100)[M] +, 225(75), 207(4), 196(70), 177(20), 151(4). (3p) 6 H 3 CO 2 C Cl White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.03 (d, J = 7.2 Hz, 2H), 7.56 (d, J = 7.2 Hz, 2H), 7.46 (d, J = 6.8 Hz, 2H), 7.35 (d, J = 7.6 Hz, 2H), 7.17 (d, J = 16.4 Hz, 1H), 7.09 (d, J = 16.4 Hz, 1H), 3.93 (s, 3H) ; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , MS (EI) m/z (%): 272(85)[M] +, 241(47), 213(9), 178(100), 152(12). (3q) 6 H 3 CO 2 C Br Yellow solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.03 (d, J = 7.6 Hz, 2H), 7.56 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 8.0 Hz, 2H), (dd, J = 18.4 Hz, J = 16.4 Hz, 2H), 3.93 (s, 3H) ; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , MS (EI) m/z (%): 316(58)[M-1] +, 285(29), 258(4), 205(4), 192(4), 178(100), 152(15). (3r) 6 S8

9 H 3 CO 2 C CH 3 White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.02 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 7.6 Hz, 2H), 7.43 (d, J = 7.6 Hz, 2H), (m, 3H), 7.08 (d, J = 16.4 Hz, 1H), 3.92 (s, 3H), 2.37 (s, 3H) ; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , 52.16, MS (EI) m/z (%): 252(100)[M] +, 221(36), 193(37), 178(94), 152(10). (3s) 10 H 3 CO 2 C OCH 3 White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.01 (d, J = 8.0 Hz, 2H), 7.54 (d, J = 8 Hz, 2H,), 7.48 (d, J = 8.4 Hz, 2H), 7.18 (d, J = 16.4 Hz, 1H), (dd, J = 8 Hz, J = 16.4 Hz, 3H), 3.92 (s, 3H), 3.84 (s, 3H),; 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , 55.48, 52.18,. MS (EI) m/z (%): 268(100)[M] +, 273(19), 209(10), 194(20), 178(18), 165(50), 152(5). (3t) 11 H 3 CO 2 C t Bu White solid, mp C. 1 H NMR (400 MHz, CDCl 3, TMS) δ 8.02 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.4 Hz, 2H), 7.48 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 2H), Hong F.-J., Low Y. Y., Chong K. W., et al. The Journal of Organic Chemistry, 2014, 79(10): Jana D., Ghorai B. K. Tetrahedron, 2012, 68(36): S9

10 (d, J = 16.4 Hz, 1H), 7.09 (d, J = 16.4 Hz, 1H), 3.92 (s, 3H), 1.34 (s, 9H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , 52.20, 34.83, MS (EI) m/z (%): 294(155)[M] +, 279(100), 263(5), 247(15), 220(5), 191(5), 178(20). S10

11 5. Copies of 1H and 13C NMR spectra of products 3a-3t NC 3a S11

12 NC 3a S12

13 H 3 CO 2 C 3b S13

14 H 3 CO 2 C 3b S14

15 F 3 C 3c S15

16 F 3 C 3c S16

17 F 3d S17

18 F 3d S18

19 Cl 3e S19

20 Cl 3e S20

21 Br 3f S21

22 Br 3f S22

23 3g S23

24 3g S24

25 3h NC S25

26 3h NC S26

27 3i F S27

28 3i F S28

29 3j Cl S29

30 3j Cl S30

31 3k H 3 CO S31

32 3k H 3 CO S32

33 CO 2 CH 3 3l S33

34 CO 2 CH 3 3l S34

35 H 3 CO OCH 3 3m H 3 CO S35

36 H 3 CO OCH 3 3m H 3 CO S36

37 3n S37

38 3n S38

39 H 3 CO 2 C 3o F S39

40 H 3 CO 2 C 3o F S40

41 H 3 CO 2 C 3p Cl S41

42 H 3 CO 2 C 3p Cl S42

43 H 3 CO 2 C 3q Br S43

44 H 3 CO 2 C 3q Br S44

45 H 3 CO 2 C 3r CH 3 S45

46 H 3 CO 2 C 3r CH 3 S46

47 H 3 CO 2 C 3s OCH 3 S47

48 H 3 CO 2 C 3s OCH 3 S48

49 H 3 CO 2 C 3t t Bu S49

50 H 3 CO 2 C 3t t Bu S50

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