Synfacts 2021; 17(02): 0159
DOI: 10.1055/s-0040-1719317
Metals in Synthesis

Nickel-Catalyzed Enantioselective 1,1-Arylboration of Unactivated Olefins

Contributor(s):
Mark Lautens
,
Austin D. Marchese
Wang W, Ding C, Yin G. * Wuhan University, P. R. of China
Catalyst-Controlled Enantioselective 1,1-Arylboration of Unactivated Olefins.

Nat. Catal. 2020;
3: 951-958
DOI: 10.1038/s41929-020-00523-8.
 

Significance

An enantioselective method for the 1,1-arylboration of unactivated olefins using a simple nickel-diamine catalyst is reported. A range of olefins were employed from ethylene and propylene to olefins containing tethered Lewis basic ­heteroatoms or reactive 1° alkyl halides.


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Comment

The regioselectivity of the reaction was demonstrated to be catalyst controlled. A mechanism involving an initial 1,2-insertion of a Ni–Bpin species is reported. The proposed catalytic cycle was supported by a variety of mechanistic studies including a deuterium labeling study.


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Publication History

Publication Date:
20 January 2021 (online)

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