Catalyst-Dependent Divergent Synthesis of Pyrroles from 3-Alkynyl Imine Derivatives: A Noncarbonylative and Carbonylative Approach

A novel Ru0‐ and RhI‐catalyzed noncarbonylative and carbonylative cycloisomerization of readily available 3‐alkynyl imine derivatives has been developed to provide 3,4‐fused or nonfused pyrrole derivatives efficiently in moderate to excellent yields. The key steps involve the formation of a rutheniu...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-08, Vol.53 (32), p.8492-8497
Main Authors: Chen, Gen-Qiang, Zhang, Xiao-Nan, Wei, Yin, Tang, Xiang-Ying, Shi, Min
Format: Article
Language:English
Subjects:
Carbon monoxide
Carbonyls
CC bond activation
Derivatives
Imines
Isomerization
Ligands
pyrrole synthesis
Pyrroles
rhodium
ring expansion
Ruthenium
Synthesis
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Summary:A novel Ru0‐ and RhI‐catalyzed noncarbonylative and carbonylative cycloisomerization of readily available 3‐alkynyl imine derivatives has been developed to provide 3,4‐fused or nonfused pyrrole derivatives efficiently in moderate to excellent yields. The key steps involve the formation of a ruthenium carbenoid intermediate or a rhodacycle intermediate, respectively. In these reactions, CO can serve as a ligand or a reagent. Carbonylation or not: A novel Ru0‐ and RhI‐catalyzed noncarbonylative and carbonylative synthesis of multisubstituted pyrroles from readily available 3‐alkynyl imine derivatives has been developed. The key steps involve an oxidative addition and a 1,2‐alkyl shift, respectively.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201405215