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Synlett 2009(15): 2529-2533  
DOI: 10.1055/s-0029-1217743
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Polysubstituted Pyrroles via PhI(OAc)2-Mediated Oxidative Coupling of Enamine Esters and Ketones

Jun-Yan Wang, Su-Ping Liu, Wei Yu*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
e-Mail: yuwei@lzu.edu.cn.;
Further Information

Publication History

Received 1 April 2009
Publication Date:
27 August 2009 (online)

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Abstract

Enamine esters or ketones could undergo homocoupling by the action of (diacetoxyiodo)benzene in the presence of BF3˙OEt2, giving rise to pyrrole products. This reaction could be used to synthesize symmetric polysubstituted pyrroles. Some asymmetric polysubstituted pyrroles could also be prepared using this protocol.

Key words

(diacetoxyiodo) benzene - oxidative coupling - enamine esters - pyrroles

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15

Procedures for the Preparation of Asymmetric Pyrroles BF3˙OEt2 (0.04 mmol) was added to a solution of 3-alkyl-enamine esters (0.2 mmol) and 3-phenyl-enamine esters
(1.2 mmol) in 1 mL CH2Cl2, followed by DIB (0.22 mmol), and the mixture was stirred at 0-10 ˚C. After the reaction finished as indicated by TLC, the mixture was concentrated under reduced pressure, and the residue was treated with flash column chromatography to give the product.