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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 14.

Vinylation using 20 and 23 in NaOH–H₂O



Entry	R¹	R²	X	Pd cat (mol%)	Heat source	t/min	Yield (%)
1	Me	4-MeC(O)	Br	Pd(OAc)₂ (0.5)	µW	10	97
2	Et	4-MeC(O)	Br	24 (0.5)	µW	10	90
3	Me	4-MeC(O)	Br	24 (0.1)^a	µW	10	99
4	Me	4-MeO	I	24 (0.1)	µW	10	93
5	Me	4-MeO	I	24 (0.01)^a	Δ	240	89
6	Me	3,5-(MeO)₂	I	Pd(OAc)₂ (0.1)^a	µW	15	83
7	Me	4-MeO	Br	24 (1)^a	µW	10	97
8	Me	^b	Br	24 (1)^a	µW	20	92
9	Me	4-Cl	Br	24 (1)^a	µW	15	71
10	Me	^c	Br	Pd(OAc)₂ (0.5)^d	Δ	^e	89
11	Me	^c	Br	Pd(OAc)₂ (0.5)^a	µW	10	89
12	Me	^f	Br	24 (1)^a	µW	15	97
13	Me	4-MeC(O)	Cl	24 (2)^a	µW	25	71
14	Me	4-PhC(O)	Cl	24 (2)^a	µW	25	65

^a

TBAB (25 mol%) added.

^b

1-Bromonaphthalene.

^c

2-Bromo-6-methoxynaphthalene.

^d

TBAB (200 mol%).

^e

1 day.

^f

3-Bromopyridine.