Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Overview

Journal Chem

Publisher Elsevier

Date 2020 Jul 21

PMID 32685767

Citations 6

Authors

Xiaojun Zeng

Shiwen Liu

Yuhao Yang

Yi Yang

Gerald B Hammond

Bo Xu

Affiliations

Soon will be listed here.

Abstract

We describe a catalyst-free 1,2--dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system-a combination of NXS electrophile and alkali metal halide (MX) in acetic acid-is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the generation of XX electrophile, including ICl, IBr, BrCl, I and Br.

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