Table 1.

Development of a Phosphonium Salt Alkylation Reaction

entry	catalyst system	additive	temp °C	yield 2aa	yield 3a
1	Ni(COD)2, SIPr·HCl NaOtBu	-	50	37%	20%
2	Ni(COD)2, PCy3	-	50	45%	20%
3	Ni(COD)2, di-tBubpy	-	50	37%	22%
4	Pd(OAc)2, SIMesr·HCl NaOtBu	-	50	3%	2%
5	Pd(OAc)2, PCy3,	-	50	8%	3%
6	Co(acac)3, L1	-	50	10%	<1%
7	Co(acac)3, L1	-	23	12%	<1%
8	Co(acac)3, L2	-	23	47%	<1%
9	Co(acac)3, L2	N-Me imidazole	23	67%	<1%
10	Co(acac)3, L2	ZnCl2	23	26%	<1%
11b	Co(acac)3, L2	N-Me imidazole	23	79%	<1%
12b	Co(acac)3, L3	N-Me imidazole	23	86% (78%)c	<1%

^aYields calculated by GC using 1,3,5-trimethoxybenzene as a standard. THF concentration 0.1 M.

^bTHF concentration 0.033 M.

^cIsolated yield.