Xiaojun Zeng1, Shiwen Liu2, Yuhao Yang1, Yi Yang2, Gerald B Hammond1,3, Bo Xu2. 1. Department of Chemistry, University of Louisville, Louisville, KY 40292, USA. 2. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China. 3. Lead Contact.
Abstract
We describe a catalyst-free 1,2-trans-dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system-a combination of NX1S electrophile and alkali metal halide (MX2) 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 in-situ generation of X1X2 electrophile, including ICl, IBr, BrCl, I2, and Br2.
We describe a catalyst-free 1,2-trans-dihalogenation of pan class="Chemical">alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system-a combination of NX1S electrophile and alkali metal halide (MX2) 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 in-situ generation of X1X2 electrophile, including ICl, IBr, BrCl, I2, and Br2.
Authors: S Desrat; C Remeur; C Gény; G Rivière; C Colas; V Dumontet; N Birlirakis; B I Iorga; F Roussi Journal: Chem Commun (Camb) Date: 2014-08-11 Impact factor: 6.222
Authors: Vinayak Agarwal; Zachary D Miles; Jaclyn M Winter; Alessandra S Eustáquio; Abrahim A El Gamal; Bradley S Moore Journal: Chem Rev Date: 2017-01-20 Impact factor: 60.622