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Iron‐Catalyzed Direct Diazidation for a Broad Range of Olefins
Author(s) -
Yuan YongAn,
Lu DengFu,
Chen YunRong,
Xu Hao
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507550
Subject(s) - catalysis , vicinal , olefin fiber , chemistry , combinatorial chemistry , lewis acids and bases , redox , lewis acid catalysis , primary (astronomy) , organic chemistry , physics , astronomy
Reported herein is a new iron‐catalyzed diastereoselective olefin diazidation reaction which occurs at room temperature (1–5 mol % of catalysts and d.r. values of up to >20:1). This method tolerates a broad range of both unfunctionalized and highly functionalized olefins, including those that are incompatible with existing methods. It also provides a convenient approach to vicinal primary diamines as well as other synthetically valuable nitrogen‐containing building blocks which are difficult to obtain with alternative methods. Preliminary mechanistic studies suggest that the reaction may proceed through a new mechanistic pathway in which both Lewis acid activation and iron‐enabled redox‐catalysis are crucial for selective azido‐group transfer.