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Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

ABSTRACT: We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

SUBMITTER: Li H

PROVIDER: S-EPMC6677148 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Li Hongze H Shen Shou-Jie SJ Zhu Cheng-Liang CL Xu Hao H

Journal of the American Chemical Society 20190530 23

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby pro ...[more]

PMID: 31070901

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