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. Author manuscript; available in PMC: 2009 Jul 27.
Published in final edited form as: Chem Commun (Camb). 2008 Aug 27;(1):20–33. doi: 10.1039/b809676g

Table 8.

Vinylation using 1-methyl-1-vinysiletane (15)

graphic file with name nihms92008t8.jpg
Entry R 15
(equiv.)		 TBAF
(equiv.)		 Pd(dba)2
(mol%)		 t/h Yield (%)
1 4-COOEt 1.2 2.0 1 1 93
2 4-C(O)Me 1.2 2.0 1 1 85
3 4-C(O)Mea 1.2 3.0 2.5b 0.5c 75
4 4-NO2 1.2 2.0 1 1 90
5 4-CN 1.2 2.0 1 1 87
6 4-OMe 1.5 4.5 5d 4 74
7 3-NO2 1.2 2.0 1 1 92
8 3-COOEt 1.2 2.0 3 1 90
9 3-CH2OH 1.2 2.0 5d 7.5 79
10 2-NO2 1.2 2.0 1 1.5 86
11 2-COOEt 1.2 3.0 5d 14 85
12 2-Me 1.2 3.0 5d 16 70
13 2-OMe 1.5 4.5 5d 10 75
14 e 1.2 3.0 5 4 76
a

4-Bromoacetophenone used as substrate.

b

[allylPdCl]2 (2.5 mol%) used as catalyst.

c

40 °C.

d

AsPh3 (10 mol%) added to the reaction.

e

1-Iodonaphthalene used as substrate.