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. Author manuscript; available in PMC: 2014 Aug 2.
Published in final edited form as: Org Lett. 2013 Jul 23;15(15):3950–3953. doi: 10.1021/ol401727y

Table 2.

Survey of cross-coupling partners.agraphic file with name nihms-508899-t0003.jpg

entry X yield (t-amyl alcohol)b yield (2-Me-THF)b,c
1 OSO2NMe2 100 100
2 OCONEt2 57 50
3 OPiv 94 100
4 OMs 97 95
5 OTs 100 98
6 OTf 100 100
7 Cl 100 94
8 Br 97 92
9 I 100 97
a

Conditions: NiCl2(PCy3)2 complex (5 mol %), substrate (1.00 equiv), 2 (2.50 equiv), K3PO4 (4.50 equiv), hexamethylbenzene (0.10 equiv), 100 °C, 12 h.

b

Yield of 3 determined by 1H NMR analysis of the crude reaction mixtures using hexamethylbenzene as an internal standard.

c

66 °C