Stereoselective alkoxycarbonylation of unactivated C(sp3)–H bonds with alkyl chloroformates via Pd(II)/Pd(IV) catalysis

Gang Liao, Xue-Song Yin, Kai Chen, Qi Zhang, Shuo-Qing Zhang and Bing-Feng Shi ()
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Gang Liao: Zhejiang University
Xue-Song Yin: Zhejiang University
Kai Chen: California Institute of Technology
Qi Zhang: Zhejiang University
Shuo-Qing Zhang: Zhejiang University
Bing-Feng Shi: Zhejiang University

Nature Communications, 2016, vol. 7, issue 1, 1-9

Abstract: Abstract Several examples on Pd-catalysed carbonylation of methyl C(sp3)–H bonds with gaseous CO via Pd(II)/Pd(0) catalysis have been reported. However, methylene C(sp3)–H carbonylation remains a great challenge, largely due to the lack of reactivity of C–H bonds and the difficulty in CO migratory insertion. Herein, we report the stereoselective alkoxycarbonylation of both methyl and methylene C(sp3)–H bonds with alkyl chloroformates through a Pd(II)/Pd(IV) catalytic cycle. A broad range of aliphatic carboxamides and alkyl chloroformates are compatible with this protocol. In addition, this process is scalable and the directing group could be easily removed under mild conditions with complete retention of configuration.

Date: 2016
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DOI: 10.1038/ncomms12901

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