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. Author manuscript; available in PMC: 2008 Oct 18.
Published in final edited form as: J Am Chem Soc. 2007 Jul 12;129(31):9602–9603. doi: 10.1021/ja074008l

Table 1.

Alkyl-Alkyl Suzuki Cross-Coupling of an Unactivated Secondary Alkyl Bromide: Effect of Reaction Parameters graphic file with name nihms-58406-f0004.jpg

entry variation from the “standard” conditions yield (%) a
1 none 83
2 bathophenanthroline, instead of 1 25
3 trans-2-aminocyclohexanol, instead of 1 <5
4 prolinol, instead of 1 <5
5 s-Bu-Pybox, b instead of 1 7
6 trans-1,2-cyclohexanediamine, instead of 1 53
7 trans-N,N,N’,N’-tetramethyl-1,2-cyclohexanediamine, instead of 1 <5
8 cis isomer of 1, instead of 1 46
9 N,N’-dimethylethylenediamine, instead of 1 7
10 no 1 <5
11 no NiCl2·glyme <5
12 NiBr2·diglyme, instead of NiCl2·glyme 81
13 Ni(cod)2, instead of NiCl2·glyme 75
14 NiCl2, instead of NiCl2·glyme <5
15 THF, instead of dioxane 80
16 toluene, instead of dioxane 47
17 Et2O, instead of dioxane <5
18 3% NiCl2·glyme and 4% 1, instead of 6% NiCl2·glyme and 8% 1 56
19 no KOt-Bu <5
20 no i-BuOH <5
a

Determined by GC analysis versus a calibrated internal standard (average of two experiments).

b

s-Bu-Pybox = (S,S)-2,6-bis(4-(2- butyl)-2-oxazolin-2-yl)pyridine.