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

doi:10.1021/ol1025348

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

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93 Citations (SciVal)

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 language	English
Pages (from-to)	5740-5743
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	24
Early online date	15 Nov 2010
DOIs	https://doi.org/10.1021/ol1025348
Publication status	Published - 17 Dec 2010

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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.",

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AU - Taylor, James E

AU - Jones, Matthew

AU - Williams, Jonathan M J

AU - Bull, Steven D

PY - 2010/12/17

Y1 - 2010/12/17

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/78650336304

U2 - 10.1021/ol1025348

DO - 10.1021/ol1025348

M3 - Article

SN - 1523-7060

VL - 12

SP - 5740

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JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

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

Abstract

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