Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
Open Access
- 17 January 2013
- Vol. 18 (1), 1188-1213
- https://doi.org/10.3390/molecules18011188
Abstract
Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.Keywords
This publication has 110 references indexed in Scilit:
- ChemInform Abstract: A Simple, Efficient, and Recyclable Phosphine-Free Catalytic System for Carbonylative Suzuki Coupling Reaction of Aryl and Heteroaryl Iodides.ChemInform, 2011
- Domino approach to 2-aroyltrimethoxyindoles as novel heterocyclic combretastatin A4 analoguesEuropean Journal of Medicinal Chemistry, 2011
- Crystal Structures of TbCatB and Rhodesain, Potential Chemotherapeutic Targets and Major Cysteine Proteases of Trypanosoma bruceiPLoS Neglected Tropical Diseases, 2010
- A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P)Expert Opinion on Investigational Drugs, 2009
- Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatBBioorganic & Medicinal Chemistry Letters, 2008
- A Unique Catalyst Effects the Rapid Room-Temperature Cross-Coupling of Organozinc Reagents with Carboxylic Acid Fluorides, Chlorides, Anhydrides, and ThioestersJournal of the American Chemical Society, 2004
- Palladium-Catalyzed Carbonylative Cross-Coupling of Organoboranes with Hypervalent Iodonium Salts: Synthesis of Aromatic KetonesSynthetic Communications, 1998
- New Cobalt‐ and Iron‐Catalyzed Reactions of Organozinc compoundsAngewandte Chemie, 1996
- Directed ortho metalation of N,N-diethylbenzamides. Silicon protection of ortho sites and the o-methyl groupThe Journal of Organic Chemistry, 1989
- The Reaction of the Chloromagnesium Derivative of Chloromagnesium Phenylacetate with Isocyanates, Carbamyl Chlorides and IsothiocyanatesJournal of the American Chemical Society, 1955