Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane

Toshifumi Dohi; Koji Morimoto; Akinobu Maruyama; Yasuyuki Kita

doi:10.1021/ol060333m

Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane

Org Lett. 2006 May 11;8(10):2007-10. doi: 10.1021/ol060333m.

Authors

Toshifumi Dohi¹, Koji Morimoto, Akinobu Maruyama, Yasuyuki Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan.

PMID: 16671768
DOI: 10.1021/ol060333m

Abstract

[reaction: see text] The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), mediates the unprecedented, oxidative coupling reaction of pyrroles to give alpha-linked bipyrroles selectively in the presence of bromotrimethylsilane. This straightforward synthesis could provide 2,3'-bipyrrole by the choice of a N-substituent of pyrrole. Mechanistic consideration of the present reaction is also described.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Combinatorial Chemistry Techniques*
Hydrocarbons, Halogenated / chemistry*
Molecular Structure
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Silanes / chemistry*

Substances

Hydrocarbons, Halogenated
Pyrroles
Silanes