One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

Organic Letters
Abdusalom A SuleymanovKay Severin

Abstract

A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.

References

Sep 26, 2002·Angewandte Chemie·David B Kimball, Michael M Haley
Apr 9, 2004·Organic Letters·Antoni KrasińskiK Barry Sharpless
Dec 17, 2008·Organic Letters·Zheng-Hui GuanXumu Zhang
Jul 25, 2012·Nature Chemistry·Ana-Florina VoicaPhil S Baran
Apr 23, 2013·Angewandte Chemie·Chengming WangYong Huang
May 14, 2014·The Journal of Organic Chemistry·Huan SunYong Huang
Oct 23, 2014·Angewandte Chemie·Gregor KieferKay Severin
Nov 5, 2014·Angewandte Chemie·Hai T Dao, Phil S Baran
Apr 8, 2015·Organic & Biomolecular Chemistry·Wanfang Li, Xiao-Feng Wu
Jun 25, 2015·Chemical Society Reviews·Kay Severin
Sep 17, 2015·Angewandte Chemie·Florian G PerrinKay Severin
Jul 12, 2017·Angewandte Chemie·David KosslerNicolai Cramer

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Citations

Apr 2, 2019·Chemistry : a European Journal·Abdusalom A SuleymanovKay Severin
Sep 10, 2019·Angewandte Chemie·Abdusalom A SuleymanovKay Severin

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