. Author manuscript; available in PMC: 2013 Nov 16.

Published in final edited form as: J Org Chem. 2012 Nov 6;77(22):9989–10000. doi: 10.1021/jo302086g

Table 2.

Allylation of a variety of aryl halides^a


Entry	X	product	yield^b
1	I	(3a) 1 mmol scale, set up in glovebox	88
2	I	10 mmol scale, set up on benchtop^c	81
3	I	R = C(O)Me (3b)	71
4	I	R = CHO (3c)	70
5	I	R = NHTs (3d)	73
6	I	R = NHC(O)CF₃ (3e)	64
7	I	R = CH₂OTBS (3f)	80^d
8	I	R = NMe₂ (3g)	55
9	I	R = Me (3h)	86
10	I	R = OMe (3i)	83
11	I	R = Br (3j)	64^e
12	Br	R = CO₂Me (3k)	65
13	Br	R = C(O)Me (3b)	48
14	Br	R = CF₃ (3l)	51^f
15	Br	R = CN (3m)	77
16	I	(3n)	78
17	I	R = CN (3o)	86
18	I	R = OMe (3p)	80

As in Table 1, but on 1 mmol scale in 2 mL of THF/NEP. Reaction times were 15–24 h.

Yield after purification. For complete selectivity data, see Tables S1 and S2 in the Supporting Information.

A 1 mmol-scale reaction run on the benchtop (Procedure B) gave an 82% GC yield.

Reaction was run on a 0.5 mmol scale.

NMR yield of 3j. Isolated product is contaminated with 9% of 3a from hydrodeiodination.

Yield is an average of two runs, one at 0.5 mmol scale and one at 1 mmol scale.