Nature Communications

Table 1 Nickel-catalyzed hydroalkylation of alkynes: optimization of conditions

From: Regio‐ and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes


Entry	Ni cat.	Ligand	Solvent	T /˚C	Yield^a/%	ee^c/%
1	NiBr₂•DME	L6	DMAc	40	8	85
2	NiCl₂•DME	L6	DMAc	40	27	88
3	NiCl₂	L6	DMAc	40	20	87
4	NiCl₂•DME	L6	NMP	40	37	89
5	NiCl₂•DME	L6	DMF	40	5	77
6	NiCl₂•DME	L6	THF	40	26	80
7	NiCl₂•DME	L6	NMP	20	45	95
8	NiCl₂•DME	L6	NMP	0	52	96
9	NiCl₂•DME	L6	NMP/THF (7/1)	0	61	95
10	NiCl₂•DME	L6	NMP/THF (4/1)	0	70	96
11	NiCl₂•DME	L6	NMP/THF (2/1)	0	71^b	97

DMAc dimethylacetamide, NMP N-methyl-2-pyrrolidone, DMF N,N-dimethylformamide, THF tetrahydrofuran, ee enantiomer excess.
^aIsolated yields were given.
^bSingle r.r.
^cThe ee values were determined by HPLC on a chiral stationary phase.

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