. Author manuscript; available in PMC: 2011 Nov 28.

Published in final edited form as: Chem Asian J. 2011 Mar 8;6(7):1860–1875. doi: 10.1002/asia.201000875

Table 5.

Ni-Catalyzed Allylic Substitution of Alkenes

graphic file with name nihms-308263-t0028.jpg

Entry	x	y¹	y²	R¹ (Product)	yield (%)^[a]
1^[b]	10	20	0	Me (5a)	77 (71)^[c]
2	10	10	10	nC₆H₁₃ (5b)	79
3	20	20	20	CH₂OSiEt₃ (5c)	73
4	10	10	10	(CH₂)₂OTBS (5d)	83^[d]
5	20	20	20	CH₂CHMe₂ (5e)	87
6^[e]	20	40	0	cyclohexyl (5f)	64^[f]
7	20	40	0	14	25

^[a]

Isolated yield; E/Z selectivity >98:2 in all cases.

^[b]

Propylene pressure 1 atm (balloon); toluene (0.2 M).

^[c]

5 mol% Ni(cod)₂, 10 mol% PCy₂Ph.

^[d]

Yield of free alcohol after treatment with 1 N HCl.

^[e]

Et₃SiOTf added over 4 h.

^[f]

Yield includes trace amounts of regioisomers (total <8%).

[f]