BCl3 catalyzed Z-selective intramolecular chlorocarbamoylation of alkynes/allenes

Zhantao Yang; Linlin Chen; Yuhang Zhao; Qianhui Chen; Wanjun Zhao; Linfei Li; Boxuan Zhang; Hua Xie; Xiangtao Kong; Chun-Hua Yang

doi:10.1039/D4QO01487A

BCl₃ catalyzed Z-selective intramolecular chlorocarbamoylation of alkynes/allenes†

Zhantao Yang,

^a Linlin Chen,^a Yuhang Zhao,^a Qianhui Chen,^a Wanjun Zhao,^a Linfei Li,^a Boxuan Zhang,^a Hua Xie,

^b Xiangtao Kong

*^a and Chun-Hua Yang

*^a

Author affiliations

* Corresponding authors

^a Henan Key Laboratory of New Opto-electronic Functional Materials, College of Chemistry and Chemical Engineering, Anyang Normal University, 436 Xian'ge Road, Anyang 455000, People's Republic of China
E-mail: 09yangchunhua@163.com

^b State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

Abstract

A metal-free stereoselective intramolecular chlorocarbamoylation of alkynes/allenes driven by BCl₃ was described, which provides a general and practical method for constructing versatile and chlorinated methylene lactams or tetrahydroisoquinolinones with (Z) geometry at the double bond, featuring a stereochemically defined tetrasubstituted chloroethene.

Organic Chemistry Frontiers

BCl₃ catalyzed Z-selective intramolecular chlorocarbamoylation of alkynes/allenes†

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Organic Chemistry Frontiers