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Synthesis of 3-Substituted Isocoumarins via a Cascade Intramolecular Ullmann-Type Coupling–Rearrangement Process

Zhi-Yuan Ge, Xiang-Dong Fei, Ting Tang, Yong-Ming Zhu* and Jing-Kang Shen*

*College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, People’s Republic of China, Email: zhuyongmingsuda.edu.cn, jkshenmail.shcnc.ac.cn

Z.-Y. Ge, X.-D. Fei, T. Tang, Y.-M. Zhu, J.-K. Shen, J. Org. Chem., 2012, 77, 5736-5743.

DOI: 10.1021/jo300916s (free Supporting Information)


Abstract

A simple and highly efficient strategy for the synthesis of 3-substituted isocoumarins from 1-(2-halophenyl)-1,3-diones is based on a cascade copper(I)-catalyzed intramolecular Ullmann-type C-arylation and rearrangement process. This methodology tolerates a wide range of substrates and is applicable to library synthesis.


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Key Words

Isocoumarins


ID: J42-Y2012-2150