Issue 13, 2013

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

Abstract

An operationally simple and practical protocol for the synthesis of (E)-α-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)-α-chloro and (E)-α-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)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C–S bond with Grignard reagents.

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Nov 2012
Accepted
26 Jan 2013
First published
29 Jan 2013

Org. Biomol. Chem., 2013,11, 2175-2185

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

Z. Yang, X. Chen, W. Kong, S. Xia, R. Zheng, F. Luo and G. Zhu, Org. Biomol. Chem., 2013, 11, 2175 DOI: 10.1039/C3OB27307E

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