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Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Hongze LiShou-Jie ShenCheng-Liang ZhuHao Xu
Published in: Journal of the American Chemical Society (2019)
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.
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