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Synfacts 2018; 14(12): 1255
DOI: 10.1055/s-0037-1611312
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Enantioselective Reductive Diarylation

Contributor(s):
Mark Lautens
,
Christian Dank
Wang K, Ding Z, Zhou Z, Kong W. * Wuhan University, P. R. of China
Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling.

J. Am. Chem. Soc. 2018;
140: 12364-12368
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Publication History

Publication Date:
19 November 2018 (online)

 
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Key words

nickel catalysis - domino reaction - diarylation

Significance

The authors report a reductive di­arylation of alkenes by using a nickel-catalyzed domino process employing two aryl electrophiles. This represents the first report of metal-catalyzed reductive coupling for the synthesis of oxindole scaffolds.


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Comment

Following optimization of the reaction conditions, a broad substrate scope that included aryl bromides and alkenes was observed. An example of an azaoxindole was also demonstrated. The authors consider two possible pathways: One features two oxidative addition steps. The key step of the second pathway is a transmetalation between two nickel(II) species.


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