Combination of a Cyano Migration Strategy and Alkene Difunctionalization: The Elusive Selective Azidocyanation of Unactivated Olefins

Zhen Wu; Rongguo Ren; Chen Zhu

doi:10.1002/anie.201605130

Combination of a Cyano Migration Strategy and Alkene Difunctionalization: The Elusive Selective Azidocyanation of Unactivated Olefins

Angew Chem Int Ed Engl. 2016 Aug 26;55(36):10821-4. doi: 10.1002/anie.201605130. Epub 2016 Aug 4.

Authors

Zhen Wu¹, Rongguo Ren¹, Chen Zhu^{2

3}

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
² Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China. chzhu@suda.edu.cn.
³ Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. chzhu@suda.edu.cn.

PMID: 27490333
DOI: 10.1002/anie.201605130

Abstract

A conceptually new, efficient, and metal-free approach for the challenging azidocyanation of unactivated alkenes is presented. The strategy of intramolecular distal cyano migration is combined with alkene difunctionalization for the first time. A variety of useful azido-substituted alkyl nitriles are prepared in good yields and, most importantly, with exquisite regio- and stereo-selectivities.

Keywords: alkene difunctionalization; alkyl nitrile; azidocyanation; cyano migration; radical reaction.

Publication types

Research Support, Non-U.S. Gov't