Friedel-Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst

James E Taylor, Matthew Jones, Jonathan M J Williams, Steven D Bull

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) has been shown to be an effective catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles and indoles in high yields. A detailed mechanistic study implies that DBN is acting as a nucleophilic organocatalyst, with the X-ray crystal structure of a key N-acyl-amidine intermediate having been determined for the first time.
Original languageEnglish
Pages (from-to)5740-5743
Number of pages4
JournalOrganic Letters
Volume12
Issue number24
Early online date15 Nov 2010
DOIs
Publication statusPublished - 17 Dec 2010

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Amidines
Indoles
acylation
Acylation
Pyrroles
indoles
pyrroles
vehicles
Crystal structure
X-Rays
catalysts
X rays
Catalysts
crystal structure
x rays
1,5-diazabicyclo(4.3.0)non-5-ene

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Friedel-Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst. / Taylor, James E; Jones, Matthew; Williams, Jonathan M J; Bull, Steven D.

In: Organic Letters, Vol. 12, No. 24, 17.12.2010, p. 5740-5743.

Research output: Contribution to journalArticle

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