Selective divergent radical cyclization of 1,6-dienes with alkyl nitriles

Qing-Qing Kang; Yi Liu; Shi-Ping Wu; Guo-Ping Ge; Hongxing Zheng; Jun-Qi Zhang; Wen-Ting Wei

doi:10.1039/d1ob01620b

Selective divergent radical cyclization of 1,6-dienes with alkyl nitriles

Org Biomol Chem. 2021 Nov 10;19(43):9501-9505. doi: 10.1039/d1ob01620b.

Authors

Qing-Qing Kang¹, Yi Liu¹, Shi-Ping Wu¹, Guo-Ping Ge¹, Hongxing Zheng², Jun-Qi Zhang³, Wen-Ting Wei¹

Affiliations

¹ Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, China. weiwenting@nbu.edu.cn.
² Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong, 252059, China.
³ Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou, 318000, China.

PMID: 34709283
DOI: 10.1039/d1ob01620b

Abstract

An efficient, selective, and step economical radical cyclization of 1,6-dienes with alkyl nitriles initiated by α-C(sp³)-H functionalization under the Sc(OTf)₃ and Ag₂CO₃ system is described here. The selective divergent cyclization relies on the substitution effect at the α-position of the acrylamide moiety and nitriles, which is terminated by hydrogen abstraction, direct cyclization with the aryl ring, or further cyclization with the CN bond and hydrolysis, respectively.

Publication types

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