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Iodine-catalyzed diazo activation to access radical reactivity.

ABSTRACT: Transition-metal-catalyzed diazo activation is a classical way to generate metal carbene, which are valuable intermediates in synthetic organic chemistry. An alternative iodine-catalyzed diazo activation is disclosed herein under either photo-initiated or thermal-initiated conditions, which represents an approach to enable carbene radical reactivity. This metal-free diazo activation strategy were successfully applied into olefin cyclopropanation and epoxidation, and applying this method to pyrrole synthesis under thermal-initiated conditions further demonstrates the unique reactivity using this method over typical metal-catalyzed conditions.

SUBMITTER: Li P

PROVIDER: S-EPMC5958049 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Iodine-catalyzed diazo activation to access radical reactivity.

Li Pan P Zhao Jingjing J Shi Lijun L Wang Jin J Shi Xiaodong X Li Fuwei F

Nature communications 20180517 1

Transition-metal-catalyzed diazo activation is a classical way to generate metal carbene, which are valuable intermediates in synthetic organic chemistry. An alternative iodine-catalyzed diazo activation is disclosed herein under either photo-initiated or thermal-initiated conditions, which represents an approach to enable carbene radical reactivity. This metal-free diazo activation strategy were successfully applied into olefin cyclopropanation and epoxidation, and applying this method to pyrro ...[more]

PMID: 29773787

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