Jump to main content
Jump to site search

Issue 13, 2013
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Nov 2012, accepted on 26 Jan 2013 and first published on 29 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27307E
Citation: Org. Biomol. Chem., 2013,11, 2175-2185
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements