Free Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2

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1 Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan Normal University, , Ganzhou, Jiangxi, State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou , P. R. China. Phone: (+86) , fax: (+86) , Context General information 2 Typical procedure 2 Physical data for the following products 3-9 Copies of the 1 H NMR and 13 C NMR

2 Experimental Section General information: 1 H and 13 C NMR spectra were recorded on a Bruker advance Ⅲ 400 spectrometer in CDCl 3 with TMS as internal standard. Mass spectra were determined on a Hewlett Packard 5988A spectrometer by direct inlet at 70 ev. High-resolution mass spectral analysis (HRMS) data were measured on a Bruker Apex Ⅱ. All products were identified by 1 H and 13 C NMR, MS and/or HRMS. Chemicals and solvents were purchased from commercial sources. Typical procedure: TBHP ( M in decane, 1.0 mmol) was added to a solution of phenyl ethyne (0.5 mmol) in 10mL of ethanol, the system was heated to 120 and stirred for 15 hours. The solvent was removed under reduced pressure and column chromatographic separation gave the product of the E/Z isomer, further purification by column chromatography gave pure (E)-3a and (Z)-3a (E/Z=1:1). 2

3 Physical data for the following products All products ( 3a 3m) except for 3g are known compounds cited in the following references, and the compound 3g was confirmed by 1 H NMR, 13 C NMR, MS and HRMS analysis. References: 1. Kraus, G. A.; Watson, B. M. Tetrahedron Lett. 1996, 37, Wang, D.; Chen, D.; Haberman, J. X.; Li, C. Tetrahedron 1998, 54, Braude, E. A.; Stern, E. S. J. Chem. Soc. 1947, Nakano, T.; Umano, S.; Kino, Y.; Ishii, Y.; Ogawa, M. J. Org. Chem. 1988, 53, Li, C.; Wang, D.; Chen, D. J. Am. Chem. Soc. 1995, 117, Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc. 1959, 81, Nagashima, H.; Nakaoka, A.; Tajima, S.; Saito, Y.; Itoh, K. Chem. Lett. 1992, Masnyk, M.; Wicha, J. Tetrahedron Lett. 1988, 29, Fehr, C.; Galindo, J. Angew. Chem. Int. Ed. 2000, 39, Maleczka, R. E.; Lavis, J. M.; Clark, D. H.; Gallagher, W. P. Org. Lett. 2000, 2, Jang, Y.; Shih, Y.; Liu, J.; Kuo, W.; Yao, C. Chem. Eur. J. 2003, 9, Zhang, Y.; Li, C. Tetrahedron Lett. 2004, 45,

4 3a-(Z). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 6.52 (d, J = 11.6Hz, 1H), 5.71 (dd, J = 11.6Hz, 9.1Hz, 1H), 4.80 (dq, J = 12.5Hz, 6.3Hz, 1H), 1.73 (s, 1H), 1.38 (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 64.15, MS(EI): m/z (%): 148 (M +, 41), 133 (24), 115 (16), 105 (65), 91 (40), 77 (30), 43 (100). 3a-(E). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 6.58 (d, J = 15.9Hz, 1H), 6.28 (dd, J = 15.9Hz, 6.4Hz, 1H), (m, 1H), 2.04 (s, 1H), 1.38 (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 68.92, MS(EI): m/z (%): 148 (M +, 14), 133 (11), 115 (19), 105 (52), 91 (41), 77 (40), 43 (100). 3b-(Z). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 4H), 6.48 (d, J = 11.6Hz, 1H), 5.67 (dd, J = 11.6Hz, 9.1Hz, 1H), (m, 1H), 2.37 (s, 3H), 1.96 (s, 1H), 1.38 (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 64.18, 23.59, MS(EI): m/z (%): 162 (M +, 45), 147 (36), 129 (30), 115 (36), 105 (100), 91 (59), 77 (29), 43 (100). 3b-(E). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 4H), 6.55 (d, J = 15.9Hz, 1H), 6.23 (dd, J = 15.9Hz, 6.5Hz, 1H), 4.49 (m, 1H), 2.35 (s, 3H), 1.86 (s, 1H), (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 69.04, 23.42, MS(EI): m/z (%): 162 (M +, 71), 147 (42), 129 (27), 115 (40), 105 (100), 91 (48), 77 (20), 43 (68). 3c-(Z). F OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 4H), 6.46 (d, J = 11.6Hz, 1H), 5.69 (dd, J = 11.6Hz, 9.1Hz, 1H), 4.73 (dq, J = 12.6Hz, 6.3Hz, 1H), 1.68 (s, 1H), 1.37 (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 64.04, MS(EI): m/z (%): 166 (M +, 52), 151 (42), 133 (47), 109 (100), 96 (31), 43 (63). 4

5 OH 3c-(E). F 1 HNMR(400MHz, CDCl 3 ) δ= (m, 2H), (m, 2H), (d, J = 16.0Hz, 1H), (dd, J = 16.0Hz, 6.4Hz, 1H), (m, 1H), 1.77 (s, 1H), (d, J = 6.4Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ=163.53, , , , , , 68.83, MS(EI): m/z (%): 166 (M +, 22), 151 (35), 133 (47), 109 (100), 96 (45), 43 (53). 3d-(Z). MeO OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 4H), 6.44 (d, J = 11.6Hz, 1H), 5.61 (dd, J = 11.6Hz, 9.0Hz, 1H), (m, 1H), 3.82 (s, 3H), 1.71 (s, 1H), 1.38 (d, J = 6.3Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 64.19, 55.26, MS(EI): m/z (%): 178 (M +, 50), 163 (15), 148 (18), 135 (25), 121 (100), 108 (16), 91 (12), 77 (3), 43 (43). OH 3d-(E). MeO 1 HNMR(400MHz, CDCl 3 ) δ= (m, 4H), 6.52 (d, J = 15.9 Hz, 1H), 6.14 (dd, J = 15.9Hz, 6.6Hz, 1H), 4.48 (m, 1H), 3.82 (s, 3H), 1.67 (s, 1H), 1.38 (d, J = 6.4 Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 69.10, 55.28, MS(EI): m/z (%): 178 (M +, 33), 163 (9), 148 (3), 135 (18), 121 (100), 108 (16), 91 (17), 77 (16), 43 (31). 3e-(Z). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 6.38 (s, 1H), 4.89 (q, J = 6.5Hz, 1H), 1.93 (s, 3H), 1.65 (s, 1H), 1.35 (d, J = 6.5Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 65.55, 21.30, MS(EI): m/z (%): 162 (M +, 14), 147 (26), 129 (23), 115 (24), 105 (6), 91 (100), 77 (15), 43 (63). 3e-(E). OH 5

6 1 HNMR(400MHz, CDCl 3 ) δ=7.32 (m, 5H), 6.52 (s, 1H), 4.40 (q, J = 6.4Hz, 1H), 1.92 (s, 3H), 1.71 (s, 1H), 1.38 (d, J = 6.5 Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 73.65, 21.79, MS(EI): m/z (%): 162 (M +, 38), 147 (34), 129 (23), 115 (50), 105 (14), 91 (68), 77 (27), 43 (100). 3f-(Z). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 10H), 6.68 (s, 1H), 5.16 (q, J = 6.5Hz, 1H), 1.61 (s, 1H), 1.33 (d, J = 6.5Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , , , , , 66.05, MS(EI): m/z (%): 224 (M +, 16), 209 (4), 191 (8), 181 (100), 165 (18), 152 (10), 105 (21), 91 (29), 77 (28), 43 (46). OH 3f-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 10H), 6.71 (s, 1H), 4.68 (q, J = 6.4Hz, 1H), 1.77 (s, 1H), 1.32 (d, J = 6.4Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , , , , , 73.02, MS(EI): m/z (%): 224 (M +, 40), 191 (7), 181 (100), 166 (14), 152 (11), 105 (12), 91 (20), 77 (19), 43 (79). OH OH 3g-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 5.98 (d, J = 16.1Hz, 1H), 5.78 (dd, J = 16.1Hz, 6.1Hz, 1H), 4.34 (m, 1H), 2.19 (s, 2H), 1.66 (s, 3H), 1.28 (d, J = 6.4Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 74.08, 68.20, 29.77, MS(EI): m/z (%): 192 (M +, 0.2), 175 (7), 147 (28), 131 (47), 115 (16), 105 (18), 91 (30), 77 (23), 43 (100). HRMS (ESI): calculated for C 12 H 15 O 2 [M-H 2 O+H] + : ; found: h-(Z). HO 6

7 1 HNMR(400MHz, CDCl 3 ) δ=7.33 (m, 5H), 6.59 (d, J = 11.7Hz, 1H), 5.68 (dd, J = 11.7Hz, 9.3Hz, 1H), 4.52 (m, 1H), 1.65 (m, 3H), 0.98 (t, J = 7.5Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ=136.66, , , , , , 69.16, 30.54, MS(EI): m/z (%): 162 (M +, 28), 133 (100), 115 (43), 105 (77), 91 (84), 77 (58), 43 (29). OH 3h-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J =15.9 Hz, 1H), 6.24 (dd, J = 15.9Hz, 6.8Hz, 1H), 4.23 (m, 1H), (m, 3H), (t, J = 7.5, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 74.41, 30.22, MS(EI): m/z 162 (M +, 29), 133 (100), 115 (35), 105 (73), 91 (78), 77 (56), 43 (39). 3i-(Z). HO 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 6.58 (d, J = 11.6Hz, 1H), 5.68 (dd, J = 11.6, 9.3Hz, 1H), (dd, J = 15.5, 6.5Hz, 1H), (m, 2H), (m, 2H), (t, 3H, J =7.5). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 67.64, 39.78, 18.62, MS(EI): m/z (%): 176 (M +, 21), 133 (100), 115 (46), 105 (65), 91 (51), 77 (55), 55 (100), 43 (59). OH 3i-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J=16.0Hz, 1H), (dd, J=6.8, 15.6Hz, 1H), (m, 1H), (m, 3H), (m, 2H), (m, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 72.82, 39.77, 18.65, MS(EI): m/z (%): 176 (M +, 11), 133 (100), 115 (32), 105 (56), 91 (42), 77 (44), 43 (39). 3j-(Z). HO 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J = 11.6Hz, 1H), (dd, J = 11.6, 9.6Hz, 1H), (dd, J=9.6, 6.8Hz, 1H), (m, 1H), 1.48 (s, 1H), (d, J = 6.8Hz, 3H), (d, J= 6.8Hz, 3H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 72.55, 34.41,

8 MS(EI): m/z (%): 176 (M +, 10), 133 (100), 115 (45), 105 (26), 91 (35), 77 (28), 43 (23). OH 3j-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J = 16.3, 1H), (dd, J = 16.3, 6.8, 1H), (m, 1H), 1.60 (m, 1H), 0.98 (d, J = 5.7, 6H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 72.00, 38.87, MS(EI): m/z176 (M +, 7), 145 (100), 128 (24), 115 (24), 105 (17), 91 (62), 77 (40), 43 (62). 3k-(Z). OH 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), 6.48 (d, J = 12.7Hz, 1H), 5.78 (d, J = 12.7Hz, 1H), 1.73 (s, 1H), (s, 6H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 72.11, MS(EI): m/z 162 (M +, 22), 147 (39), 129 (18), 115 (11), 103 (16), 91 (66), 77 (23), 43 (100). OH 3k-(E). 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J = 16.0Hz, 1H), (d, J = 16.0Hz, 1H), 1.54 (s, 1H), 1.43 (s, 6H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 71.04, MS(EI): m/z 162 (M +, 12), 147 (49), 129 (29), 115 (8), 103 (11), 91 (56), 77 (28), 43 (100). 3l-(Z) O 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J=11.6Hz, 1H), (dd, J= 11.6, 8.4Hz, 1H), (m, 1H), (m, 1H), (m, 4H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 75.05, 68.06, 32.91, MS(EI): m/z (%): 174 (M +, 76), 145 (20), 131 (57), 115 (42), 104 (51), 91 (38), 77 (44), 42 (100). 3l-(E) O 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J= 15.6Hz, 1H), (dd, 8

9 J=6.4, 15.6Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 4H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 79.66, 68.16, 32.37, MS(EI): m/z (%): 174 (M +, 93), 145 (15), 131 (70), 115 (52), 104 (61), 91 (46), 77 (63), 42 (100). O O 3m-(Z) 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J=12.0Hz, 1H), (dd, J= 12.0, 7.2Hz, 1H), (m, 1H), (m, 5H), (m, 1H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , 72.17, 70.15, 66.23, MS(EI): m/z (%): 190 (M +, 11), 131 (42), 115 (14), 86 (100), 77 (22). O O 3m-(E/Z) 1 HNMR(400MHz, CDCl 3 ) δ= (m, 5H), (d, J=16.0Hz, 1H), (dd, J=6.0, 16.0Hz, 1H), (m, 1H), (m, 5H), (m, 1H). 13 CNMR(100MHz, CDCl 3 ) δ= , , , , , , 76.03, 70.91, 66.51, MS(EI): m/z (%): 190 (M +, 17), 131 (62), 115 (19), 86 (100), 77 (26). 9

10 Copies of the 1 H NMR and 13 C NMR 1 H NMR and 13 C NMR spectra of 3a-(Z): 10

11 1 H NMR and 13 C NMR spectra of 3a-(E): 11

12 1 H NMR and 13 C NMR spectra of 3b-(Z): 12

13 1 H NMR and 13 C NMR spectra of 3b-(E): 13

14 1 H NMR and 13 C NMR spectra of 3c-(Z): 14

15 1 H NMR and 13 C NMR spectra of 3c-(E): 15

16 1 H NMR and 13 C NMR spectra of 3d-(Z): 16

17 1 H NMR and 13 C NMR spectra of 3d-(E): 17

18 1 H NMR and 13 C NMR spectra of 3e-(Z): 18

19 1 H NMR and 13 C NMR spectra of 3e-(E): 19

20 1 H NMR and 13 C NMR spectra of 3f-(Z): 20

21 1 H NMR and 13 C NMR spectra of 3f-(E): 21

22 1 H NMR, 13 C NMR and HRMS spectra of 3g-(E): 22

23 23

24 1 H NMR and 13 C NMR spectra of 3h-(Z): 24

25 1 H NMR and 13 C NMR spectra of 3h-(E): 25

26 1 H NMR and 13 C NMR spectra of 3i-(Z): 26

27 1 H NMR and 13 C NMR spectra of 3i-(E): 27

28 1 H NMR and 13 C NMR spectra of 3j-(Z): 28

29 1 H NMR and 13 C NMR spectra of 3j-(E): 29

30 1 H NMR and 13 C NMR spectra of 3k-(Z): 30

31 1 H NMR and 13 C NMR spectra of 3k-(E): 31

32 1 H NMR and 13 C NMR spectra of 3l-(Z): 32

33 1 H NMR and 13 C NMR spectra of 3l-(E): 33

34 1 H NMR and 13 C NMR spectra of 3m-(Z): 34

35 1 H NMR and 13 C NMR spectra of 3m-(E): 35

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