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One‐Pot Three‐Component Catalytic Synthesis of Fully Substituted Pyrroles from Readily Available Propargylic Alcohols, 1,3‐Dicarbonyl Compounds and Primary Amines
Author(s) -
Cadierno Victorio,
Gimeno José,
Nebra Noel
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701132
Subject(s) - primary (astronomy) , chemistry , alkyne , ruthenium , amine gas treating , catalysis , ferrocene , annulation , ketone , organic chemistry , medicinal chemistry , pyrrole , combinatorial chemistry , electrochemistry , physics , electrode , astronomy
A simple and highly efficient method for the preparation of fully substituted pyrroles, from readily accessible secondary propargylic alcohols, 1,3‐dicarbonyl compounds and primary amines, has been developed. The one‐pot multicomponent reaction, which is catalysed by the system [Ru(η 3 ‐2‐C 3 H 4 Me)(CO)(dppf)][SbF 6 ]/CF 3 CO 2 H (dppf: 1,1′‐bis(diphenylphosphanyl)ferrocene), involves initial propargylation of the 1,3‐dicarbonyl compound promoted by CF 3 CO 2 H and subsequent condensation between the resulting γ‐keto alkyne and the primary amine to afford a propargylated β‐enamino ester or ketone, which undergoes a ruthenium‐catalysed 5‐ exo ‐ dig annulation to form the final pyrrole.