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Catalysts 2016, 6(11), 169; doi:10.3390/catal6110169

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

1,†
,
1,†
,
2
,
1,* and 1,3,*
1
State Key Laboratory of Bioengineering Reactor, Shanghai Key Laboratory of New Drug Design, and School of Pharmacy, East China University of Science and Technology, 130 Mei-long Road, Shanghai 200237, China
2
Shanghai Institute of Materia Medica, Shanghai 201203, China
3
Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Xiao-Feng Wu
Received: 21 September 2016 / Revised: 18 October 2016 / Accepted: 21 October 2016 / Published: 31 October 2016
(This article belongs to the Special Issue Organometallic Catalysis for Organic Synthesis)
View Full-Text   |   Download PDF [2067 KB, uploaded 31 October 2016]   |  

Abstract

The Pd(TFA)2-catalyzed [4+1] annulation of chained or cyclic α-alkenyl-dicarbonyl compounds and unprotected primary amines for “one-pot” synthesis of pyrroles is reported here. Enamination and amino-alkene were involved in this practical and efficient tandem reaction. The annulation products were isolated in moderate to excellent yields with O2 as the terminal oxidant under mild conditions. In addition, this method was applied to synthesize highly regioselective aminomethylated and di(1H-pyrrol-3-yl)methane products. View Full-Text
Keywords: Pd(TFA)2; [4+1] annulation; α-alkenyl-dicarbonyl compounds; unprotected primary amines; one-pot; tandem reaction; regio-selective Pd(TFA)2; [4+1] annulation; α-alkenyl-dicarbonyl compounds; unprotected primary amines; one-pot; tandem reaction; regio-selective
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Yu, Y.; Mang, Z.; Yang, W.; Li, H.; Wang, W. Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions. Catalysts 2016, 6, 169.

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