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. Author manuscript; available in PMC: 2009 May 26.
Published in final edited form as: Tetrahedron. 2008 May 26;64(22):5322–5327. doi: 10.1016/j.tet.2008.03.024

Table 3.

The Coupling of Vinyl (E)-TTMS-Silanes

graphic file with name nihms50827f4.jpg

entry silane R2X producta (E) yieldb (%)
1 2a PhI 5a 83
2 2a PhBr 5a 67
3 2a (4)CH3OPhI 5c 79
4 2a (4)CF3PhI 5d 90
5 2a (CH3)2C=CHBr 7a 85
6 2a iodothiophenec 8a 58
7 2a 2-iodopyridine 9a 70
8 2b PhI 5b 72
9 2b iodothiophenec 8b 66
10 2b (4)BuPhI 10b 59
11 2b 1-bromonaphthalene 11b 48
12 2b 1-iodonaphthalene 11b 70
13 2c PhBr 5c 63
14 2c PhCH=CHBrd 6ce 60
15 2d PhBr 5d 86
16 2e PhI 5e 85
17 2e PhBr 5e 72
18 2f PhI 5f 70
19 2f PhBr 5f 78
20 2g PhI 5g 84
21 2g PhBr 5g 65
22 2g (CH3)2C=CHBr 7g 50
23 2g iodothiophenec 8g 83
a

Only E-isomers were detected (1H NMR, GC-MS) except for the g series where stereochemistry is not relevant. Couplings were performed on 0.1-0.5 mmol scale of silanes (0.03 mM). Pd(PPh3)4 (10% mol).

b

Isolated yields.

c

2-Iodo-5-methylthiophene.

d

E/Z = 88:12.

e

1E/3E.