Practical pd(TFA)2-catalyzed aerobic [4+1] annulation for the synthesis of pyrroles via “one-pot” cascade reactions

Yang Yu; Zhiguo Mang; Wei Yang; Hao Li; Wei Wang

doi:10.3390/catal6110169

Practical pd(TFA)₂-catalyzed aerobic [4+1] annulation for the synthesis of pyrroles via “one-pot” cascade reactions

Yang Yu, Zhiguo Mang, Wei Yang, Hao Li, Wei Wang

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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.

Original language	English (US)
Article number	169
Journal	Catalysts
Volume	6
Issue number	11
DOIs	https://doi.org/10.3390/catal6110169
State	Published - Nov 2016
Externally published	Yes

Keywords

One-pot
Pd(TFA)
Regio-selective
Tandem reaction
Unprotected primary amines
[4+1] annulation
α-alkenyl-dicarbonyl compounds

ASJC Scopus subject areas

Catalysis
General Environmental Science
Physical and Theoretical Chemistry

Access to Document

10.3390/catal6110169

Cite this

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title = "Practical pd(TFA)2-catalyzed aerobic [4+1] annulation for the synthesis of pyrroles via “one-pot” cascade reactions",

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.",

keywords = "One-pot, Pd(TFA), Regio-selective, Tandem reaction, Unprotected primary amines, [4+1] annulation, α-alkenyl-dicarbonyl compounds",

author = "Yang Yu and Zhiguo Mang and Wei Yang and Hao Li and Wei Wang",

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T1 - Practical pd(TFA)2-catalyzed aerobic [4+1] annulation for the synthesis of pyrroles via “one-pot” cascade reactions

AU - Yu, Yang

AU - Mang, Zhiguo

AU - Yang, Wei

AU - Li, Hao

AU - Wang, Wei

PY - 2016/11

Y1 - 2016/11

N2 - 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.

AB - 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.

KW - One-pot

KW - Pd(TFA)

KW - Regio-selective

KW - Tandem reaction

KW - Unprotected primary amines

KW - [4+1] annulation

KW - α-alkenyl-dicarbonyl compounds

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