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A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis

Anon Bunrit, Supaporn Sawadjoon, Svetlana Tšupova, Per J. R. Sj÷berg and Joseph S. M. Samec*

*Department of Organic Chemistry, Stockholm University, 106 91, Stockholm, Sweden, Email: joseph.samecsu.se

A. Bunrit, S. Sawadjoon, S. Tšupova, P. J. R. Sj÷berg, J. S. M. Samec, J. Org. Chem., 2016, 81, 1450-1460.

DOI: 10.1021/acs.joc.5b02581 (free Supporting Information)


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Abstract

Pd, Ru, and Fe catalysis enable a general synthesis of 2-substituted pyrroles in overall good yields with only water and ethene as side-products. The route starts with two subsequent Pd-catalyzed monoallylations of amines with allylic alcohols. Ru-catalyzed ring-closing metathesis performed on the diallylated amines provides pyrrolines in excellent yields. By addition of ferric chloride, a selective aromatization was achieved.

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Key Words

pyrroles, RCM, ferric chloride


ID: J42-Y2016