Hydrogen-Bond-Assisted Ru(III)-Catalyzed C–C Bond Activation in 1,3-Dicarbonyls: A Direct Route to Multi-Substituted Pyrroles

Unprecedented CO-Cα bond cleavage of 1,3-dicarbonyls and enaminone, catalyzed by a well-defined Ru(III)-complex (<b>1</b>) featuring a redox-active triamine ligand (<b>L</b><sup><b>1</b></sup>) with a free -NH<sub>2</sub> arm, opening a new route to accessing substituted pyrroles with broad substrate scope and functional group tolerance in good isolated yields via multicomponent coupling of 1,3-dicarbonyls, amines, and diol, is reported. The hydrogen bonding interaction offered by <b>1</b> facilitates the formation of critical reaction intermediates, favoring the formation of pyrroles.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-07
DOI
https://doi.org/10.1021/acs.joc.5c00233
Citations
2
Primary Topic
Synthesis and Characterization of Pyrroles
Type
article
Field-Weighted Citation Impact
1.87

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article

Hydrogen-Bond-Assisted Ru(III)-Catalyzed C–C Bond Activation in 1,3-Dicarbonyls: A Direct Route to Multi-Substituted Pyrroles

Santana Chakraborty, Nanda Dulal Paul, Arijit Singha Mohapatra
2 citations
The Journal of Organic Chemistry
Synthesis and Characterization of Pyrroles
1.87
article

Hydrogen-Bond-Assisted Ru(III)-Catalyzed C–C Bond Activation in 1,3-Dicarbonyls: A Direct Route to Multi-Substituted Pyrroles

Santana Chakraborty, Nanda Dulal Paul, Arijit Singha Mohapatra
article en
2 citations

Abstract

Unprecedented CO-Cα bond cleavage of 1,3-dicarbonyls and enaminone, catalyzed by a well-defined Ru(III)-complex (<b>1</b>) featuring a redox-active triamine ligand (<b>L</b><sup><b>1</b></sup>) with a free -NH<sub>2</sub> arm, opening a new route to accessing substituted pyrroles with broad substrate scope and functional group tolerance in good isolated yields via multicomponent coupling of 1,3-dicarbonyls, amines, and diol, is reported. The hydrogen bonding interaction offered by <b>1</b> facilitates the formation of critical reaction intermediates, favoring the formation of pyrroles.

The Journal of Organic ChemistryVol. 90(15)
Indian Institute of Engineering Science and Technology, Shibpur (IN)
Science and Engineering Research Board
Openalex Percentile: Top 17%
Synthesis and Characterization of Pyrroles
1.87
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