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Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides via tert-Butyl Isocyanide Insertion

Ting Tang, Xiang-Dong Fei, Zhi-Yuan Ge, Zhong Chen, Yong-Ming Zhu* and Shun-Jun Ji*

*College of Pharmaceutical Sciences and College of Chemistry, Soochow University, Suzhou 215123, People's Republic of China, Email: zhuyongmingsuda.edu.cn, shunjunsuda.edu.cn

T. Tang, X.-D. Fei, Z.-Y. Ge, Z. Chen, Y.-M. Zhu, S.-J. Ji, J. Org. Chem., 2013, 78, 3170-3175.

DOI: 10.1021/jo4001096 (free Supporting Information)


Abstract

tert-Butyl isocyanide insertion enables a simple and efficient palladium-catalyzed carbonylative Sonogashira coupling. This methodology demonstrates the utility of isocyanides in intermolecular C-C bond construction and provides a novel pathway for the synthesis of alkynyl imines which can undergo simple silica gel catalyzed hydrolysis to afford alkynones. The approach is tolerant of a wide range of substrates and applicable to library synthesis.

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Key Words

Sonogashira Coupling, Aryl Ketones, Alkynyl Ketones, Multicomponent Reactions


ID: J42-Y2013-0800