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Synfacts 2022; 18(01): 0037
DOI: 10.1055/s-0041-1737311
Metals in Synthesis

Enantioselective Cobalt-Catalyzed Alkene Hydroalkylation

Contributor(s):
Mark Lautens
,
Alexa Torelli
Li Y, Nie W, Chang Z, Wang J.-W, Lu X, *, Fu Y. * University of Science and Technology of China and Comprehensive National Science Center, Hefei, P. R. of China
Cobalt-Catalysed Enantioselective C(sp3)–C(sp3) Coupling.

Nat. Catal. 2021;
4: 901-911
DOI: 10.1038/s41929-021-00688-w.
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Key words

cobalt catalysis - C(sp3)–C(sp3) coupling - enantioselectivity

Significance

A stereoselective Co-catalyzed C(sp3)–C(sp3) coupling reaction to access chiral fluo­roalkanes has been developed. The reaction exhibits catalyst-controlled enantioselectivity, thereby removing the requirement for substrate auxiliaries. A series of mechanistic and computational studies were conducted to elucidate the mechanism for the transformation.


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Comment

The reaction demonstrated high functional group compatibility with regards to both coupling partners. Radical clock experiments support a radical pathway from the alkyl halide. Kinetic studies suggest the reaction proceeds through an irreversible rate-limiting syn-hydrometalation of the Co–H intermediate across the π-system.


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Publication History

Article published online:
17 December 2021

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