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Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion

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

*College of Pharmaceutical Sciences and College of Chemistry, Soochow University, Suzhou, 215123, China, Email: zhuyongmingsuda.edu.cn, chemjsjsuda.edu.cn

X.-D. Fei, Z.-Y. Ge, T. Tang, Y.-M. Zhu, S.-J. Ji, J. Org. Chem., 2012, 77, 10321-10328.

DOI: 10.1021/jo302004u (free Supporting Information)


Abstract

A highly efficient palladium(0)-catalyzed strategy for the synthesis of isocoumarins involves cyclization with incorporation of tert-butyl isocyanide followed by simple acid hydrolysis to provide valuable lactones in good yields. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

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Key Words

Isocoumarins, Phthalides


ID: J42-Y2012-3670