Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Cobalt-Catalyzed Allylic C(sp3)–H Carboxylation with CO2

Cobalt-Catalyzed Allylic C(sp3)–H Carboxylation with CO2
Kenichi Michigami, Tsuyoshi Mita, Yoshihiro Sato
Catalytic carboxylation of the allylic C(sp3)–H bond of terminal alkenes with CO2 was developed with the aid of a Co/Xantphos complex. A wide range of allylarenes and 1,4-dienes were successfully transformed into the linear styrylacetic acid and hexa-3,5-dienoic acid derivatives in moderate to high yields, with excellent regioselectivity. The carboxylation showed remarkable functional group tolerability, so that selective addition to CO2 occurred in the presence of other carbonyl groups such as amide, ester, and ketone. Since styrylacetic acid derivatives can be readily converted into optically active γ-butyrolactones through Sharpless asymmetric dihydroxylation, this allylic C(sp3)–H carboxylation showcases a facile synthesis of γ-butyrolactones from simple allylarenes via short steps.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02775

DOI: 10.1021/jacs.7b02775

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