Synthesis 2014; 46(03): 281-289
DOI: 10.1055/s-0033-1338579
short review
© Georg Thieme Verlag Stuttgart · New York

Metal-Catalyzed Cross-Coupling Reactions of Halomaleic Anhydrides and Halomaleimides: Synthesis of Structurally Interesting and Biologically ­Important Natural and Unnatural Products

Prashant S. Deore*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Email: np.argade@ncl.res.in
,
Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Email: np.argade@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 31 October 2013

Accepted after revision: 06 December 2013

Publication Date:
02 January 2014 (online)


Abstract

This brief review presents a concise literature account of the metal-catalyzed cross-coupling reactions of halomaleic anhydrides and halomaleimides leading to significant synthetic and natural products. Metal-catalyzed Heck, Suzuki–Miyaura, Stille–Migita, Negishi, Hiyama, and Sonogashira cross-coupling reactions with palladium as the key element are discussed. The metal-catalyzed exchange of a vinylic leaving group by a carbon nucleophile, the SNV reaction, gives a diverse range of bioactive natural and unnatural products.