Synthesis 2018; 50(16): 3087-3113
DOI: 10.1055/s-0037-1610174
review
© Georg Thieme Verlag Stuttgart · New York

1,2-Dihaloalkenes in Metal-Catalyzed Reactions

Nicolas Gilbert
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, CP 500, Trois-Rivières, Québec, Canada   Benoit.Daoust@uqtr.ca
,
Paméla Casault
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, CP 500, Trois-Rivières, Québec, Canada   Benoit.Daoust@uqtr.ca
,
François Ladouceur
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, CP 500, Trois-Rivières, Québec, Canada   Benoit.Daoust@uqtr.ca
,
Simon Ricard
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, CP 500, Trois-Rivières, Québec, Canada   Benoit.Daoust@uqtr.ca
,
Département de Chimie, Biochimie et Physique, Université du Québec à Trois-Rivières, CP 500, Trois-Rivières, Québec, Canada   Benoit.Daoust@uqtr.ca
› Author Affiliations
This work was supported by the Université du Québec à Montréal (UQAM) and the Université du Québec à Trois-Rivières (UQTR). Simon Ricard would like to thank the FRQNT for a doctoral research scholarship. Paméla Casault would like to thank CRSNG for M.Sc. scholarship. Nicolas Gilbert would like to thank both FRQNT and CRSNG for M.Sc. scholarships.
Further Information

Publication History

Received: 27 March 2018

Accepted after revision: 02 May 2018

Publication Date:
09 July 2018 (online)


Abstract

1,2-Dihaloalkenes readily undergo simultaneous or sequential difunctionalization through transition-metal-catalyzed reactions, which makes them attractive building blocks for complex unsaturated motifs. This review summarizes recent applications of such transformations in C–C and C–heteroatom bond forming processes. The facile synthesis of stereodefined alkene derivatives, as well as aromatic and heteroatomic­ compounds, from 1,2-dihaloalkenes is thus outlined.

1 Introduction

2 Synthesis of 1,2-Dihaloalkenes

3 C–C Bond Forming Reactions

4 C–Heteroatom Bond Forming Reactions

5 Conclusion