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

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journal contribution
posted on 11.04.2017, 00:00 by 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.