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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.


 

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.


 

 

Publication History

Article published online:
17 December 2021

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