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. 2019 Aug 2;9(8):6751-6754.
doi: 10.1021/acscatal.9b01785. Epub 2019 Jul 25.

Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

Travis J DeLano  1 , Sarah E Reisman  1
Affiliations

Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

Travis J DeLano et al. ACS Catal. .

Abstract

An electrochemically-driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.

Keywords: Nickel; asymmetric catalysis; cross-coupling; electrochemistry; enantioselective.

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Figures

Figure 1.
Figure 1.
Nickel-catalyzed enantioselective electroreductive coupling. dme = 1,2-dimethoxyethane; DMA = N,N-dimethylacetamide.
Figure 2.
Figure 2.
Scope of alkenyl bromides. Reactions conducted using 0.6 mmol alkenyl bromide and 0.6 mmol benzyl chloride.
Figure 3.
Figure 3.
Scope of benzylic chlorides. Reactions conducted using 0.6 mmol alkenyl bromide and 0.6 mmol benzyl chloride.
See this image and copyright information in PMC

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