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Iron-catalyzed carboazidation of alkenes and alkynes.

ABSTRACT: Carboazidation of alkenes and alkynes holds the promise to construct valuable molecules directly from chemical feedstock therefore is significantly important. Although a few examples have been developed, there are still some unsolved problems and lack of universal methods for carboazidation of both alkenes and alkynes. Here we describe an iron-catalyzed rapid carboazidation of alkenes and alkynes, enabled by the oxidative radical relay precursor t-butyl perbenzoate. This strategy enjoys success with a broad scope of alkenes under mild conditions, and it can also work with aryl alkynes which are challenging substrates for carboazidation. A large number of diverse structures, including many kinds of amino acid precursors, fluoroalkylated vinyl azides, other specific organoazides, and 2H-azirines can be easily produced.

SUBMITTER: Xiong H

PROVIDER: S-EPMC6328574 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Iron-catalyzed carboazidation of alkenes and alkynes.

Xiong Haigen H Ramkumar Nagarajan N Chiou Mong-Feng MF Jian Wujun W Li Yajun Y Su Ji-Hu JH Zhang Xinhao X Bao Hongli H

Nature communications 20190110 1

Carboazidation of alkenes and alkynes holds the promise to construct valuable molecules directly from chemical feedstock therefore is significantly important. Although a few examples have been developed, there are still some unsolved problems and lack of universal methods for carboazidation of both alkenes and alkynes. Here we describe an iron-catalyzed rapid carboazidation of alkenes and alkynes, enabled by the oxidative radical relay precursor t-butyl perbenzoate. This strategy enjoys success ...[more]

PMID: 30631054

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