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Issue 28, 2018
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(Salen)Mn(iii)-catalyzed chemoselective acylazidation of olefins

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Abstract

We describe a (salen)Mn(III)-catalyzed three-component reaction of aldehydes, olefins, and sodium azide for the installation of two useful groups (C[double bond, length as m-dash]O and N3) into the double bond. Traditionally, (salen)Mn(III) in conjunction with iodosobenzene is a classical catalysis system for epoxidation of olefins. Owing to the highly competitive oxygenation approaches, it is a true challenge to establish a distinct strategy for the exploration of new olefin transformations based on this (salen)Mn(III) catalysis system. Herein, the key to this (salen)Mn(III)-catalyzed acylazidation of olefins was the rational application of the distinct reactivity of oxomanganese(V) species which is capable of abstracting a hydrogen atom from a substrate C–H bond. This chemoselective reaction occurred in a precisely designed reaction sequence and tolerates complex molecular structures.

Graphical abstract: (Salen)Mn(iii)-catalyzed chemoselective acylazidation of olefins

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Supplementary files

Article information


Submitted
25 Apr 2018
Accepted
18 Jun 2018
First published
19 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 6085-6090
Article type
Edge Article

(Salen)Mn(III)-catalyzed chemoselective acylazidation of olefins

L. Zhang, S. Liu, Z. Zhao, H. Su, J. Hao and Y. Wang, Chem. Sci., 2018, 9, 6085
DOI: 10.1039/C8SC01882K

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