title: Friedel-Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst.
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.
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom.
authors.forename: James E
authors.initials: JE
authors.lastname: Taylor
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Jones
authors.forename: Jonathan M J
authors.initials: JM
authors.lastname: Williams
authors.forename: Steven D
authors.initials: SD
authors.lastname: Bull
mesh_terms: D000215:Acylation; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D014046:Tolmetin / Q000138:chemical synthesis
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007211:Indoles; D011758:Pyrroles; C013554:1,5-diazabicyclo(4.3.0)non-5-ene; D014046:Tolmetin