Table 1.

Influence of Reaction Parameters on the Ni-Catalyzed Reductive Coupling of an Alkyne and Epoxide

entry	variation from standard conditions	yield (%)a	Z/Eb
1	nonec	82	90:10
2	Ni(cod)2 instead of NiBr233H2Od	82	95:5
3	NiBr23diglyme instead of NiBr233H2O	76	88:12
4	NiCl236H2O instead of NiBr233H2O	74	89:11
5	5 mol % NiBr233H2O and 20 mol %	75	95:5
	PhMe2P instead of standard catalyst/phosphine loading
7	THF instead of i-PrOH	<5e	---
8	no NiBr233H2O	<5e	---
9	30 mol % PhMe2P instead of 40 mol %	76	90:10
10	20 mol % PhMe2P instead of 40 mol %	52	91:9
11	no PhMe2P	<5e	---

^aIsolated yield of the mixture of olefin isomers.

^bDetermined by ¹H NMR spectroscopy of the crude reaction mixture.

^cComplete conversion of starting material observed within 3 h.

^dPhosphine loading was 20 mol % instead of 40 mol %.

^eDetermined by ¹H NMR spectroscopy relative to mesitylene as an internal standard.