An operationally simple approach to (E)-alpha-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

作者：Yang Zhaozhen; Chen Xiaoyi; Kong Wei; Xia Siyuan; Zheng Renwei; Luo Fang; Zhu Gangguo^*

来源：Organic and Biomolecular Chemistry, 2013, 11(13): 2175-2185.

DOI：10.1039/c3ob27307e

An operationally simple and practical protocol for the synthesis of (E)-alpha-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-alpha-chloro and (E)-alpha-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-alpha-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.

• 出版日期2013
• 单位浙江师范大学