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DOI: 10.1055/s-0033-1341214
Synthesis of Unsymmetric Aryl Aryl Ketones Using Acylindium Reagents
Unmasked Acyl Anion Equivalent from Acid Chloride with Indium: Reversed-Polarity Synthesis of Unsymmetric Aryl Aryl and Alkenyl Aryl Ketone through Palladium-Catalyzed Cross-Coupling Reaction.
Org. Lett. 2014;
16: 1144-1147
Publication History
Publication Date:
17 April 2014 (online)
Key words
acid chlorides - acylindium reagents - unsymmetric ketones - reversed-polarity synthesis - indium
Significance
Herein, a reversed-polarity synthesis of various unsymmetric aryl aryl and aryl alkenyl ketones is disclosed. By palladium-catalyzed cross-couplings of acylindium reagents, which are generated from acid chlorides by direct indium insertion, with a wide range of aryl iodides and triflates, the corresponding ketones are obtained in moderate to very good yields.
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Comment
This protocol uses very mild reaction conditions for the preparation of an unmasked acyl anion equivalent readily available from the appropriate acyl chlorides. Sensitive functional groups, such as esters, nitriles and aldehydes, are well tolerated. Most known acyl anions contain a tin, silane or zirconocene moiety and often require tedious synthetic steps for their preparation. This synthetic strategy allows a simple and straightforward access to such acyl anions by a mild indium insertion.
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