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Microwave-Promoted Tin-Free Iminyl Radical Cyclization with TEMPO Trapping: A Practical Synthesis of 2-Acylpyrroles

Yu Cai, Ankur Jalan, Aaron R. Kubosumi and Steven L. Castle*

*Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States, Email: scastlechem.byu.edu

Y. Cai, A. Jalan, A. R. Kubosumi, S. L. Castle, Org. Lett., 2015, 17, 488-491.

DOI: 10.1021/ol5035047 (free Supporting Information)


Abstract

Microwave-promoted iminyl radical cyclizations can be terminated by trapping with TEMPO, affording functionalized adducts without using toxic and hazardous reagents. The use of alkynes as radical acceptors delivers a range of 2-acylpyrroles in good yields.

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Key Words

pyrroles, TEMPO, microwave synthesis


ID: J54-Y2015