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Azido-alkynylation of alkenes through radical-polar crossover.

ABSTRACT: We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process was key to develop this transformation. A variety of homopropargylic azides possessing electron-rich and -poor aryls, heterocycles or ether substituents could be accessed in 34-84% yield. The products are synthetically useful building blocks that could be easily transformed into pyrroles or bioactive amines.

SUBMITTER: Borrel J

PROVIDER: S-EPMC10498506 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Azido-alkynylation of alkenes through radical-polar crossover.

Borrel Julien J Waser Jerome J

Chemical science 20230811 35

We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process was key to develop this transformation. A variety of homopropargylic azides possessing electron-rich and -poor aryls, heterocycles or ether substituents could be accessed in 34-84% yield. The products are synthetically useful building blocks th ...[more]

PMID: 37712015

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