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A transition-metal-free & diazo-free styrene cyclopropanation.

ABSTRACT: An operationally simple and broadly applicable novel cyclopropanation of styrenes using gem-diiodomethyl carbonyl reagents has been developed. Visible-light triggered the photoinduced generation of iodomethyl carbonyl radicals, able to cyclopropanate a wide array of styrenes with excellent chemoselectivity and functional group tolerance. To highlight the utility of our photocyclopropanation, we demonstrated the late-stage functionalization of biomolecule derivatives.

SUBMITTER: Herraiz AG

PROVIDER: S-EPMC7017872 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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A transition-metal-free & diazo-free styrene cyclopropanation.

Herraiz Ana G AG Suero Marcos G MG

Chemical science 20190828 40

An operationally simple and broadly applicable novel cyclopropanation of styrenes using <i>gem</i>-diiodomethyl carbonyl reagents has been developed. Visible-light triggered the photoinduced generation of iodomethyl carbonyl radicals, able to cyclopropanate a wide array of styrenes with excellent chemoselectivity and functional group tolerance. To highlight the utility of our photocyclopropanation, we demonstrated the late-stage functionalization of biomolecule derivatives. ...[more]

PMID: 32110302

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