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

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.

SUBMITTER: Liao G 

PROVIDER: S-EPMC5052708 | biostudies-other | 2016 Sep

REPOSITORIES: biostudies-other

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

Liao Gang G   Yin Xue-Song XS   Chen Kai K   Zhang Qi Q   Zhang Shuo-Qing SQ   Shi Bing-Feng BF  

Nature communications 20160928

Several examples on Pd-catalysed carbonylation of methyl C(sp<sup>3</sup>)-H bonds with gaseous CO via Pd(II)/Pd(0) catalysis have been reported. However, methylene C(sp<sup>3</sup>)-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(sp<sup>3</sup>)-H bonds with alkyl chloroformates through a Pd(II)/Pd(IV) catalytic cycl  ...[more]