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Pyridine‐Catalyzed Double C–N Coupling Reaction of an Isocyanate with Two Benzynes
Author(s) -
Lee YiHsien,
Chen YenChung,
Hsieh JenChieh
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101251
Subject(s) - aryne , chemistry , pyridine , isocyanate , decarboxylation , protonation , nucleophile , catalysis , medicinal chemistry , nucleophilic addition , photochemistry , organic chemistry , ion , polyurethane
Abstract A pyridine‐catalyzed double C–N bond cross‐coupling reaction involving two benzynes with an isocyanate was carried out. The coupling reaction proceeded through a unique pathway involving the formation of an unstable carbamic acid intermediate and facile decarboxylation. Subsequent nucleophilic addition/protonation of in situ prepared amines with benzynes afforded variously substituted diaryl‐ and triarylamines in moderate to good yields with tolerance of a variety of functional groups.