Rh(III)‐Catalyzed Regioselective [3+2]‐Annulation of Indoles with 1,3‐Enynes to Access 3<i>H</i>‐pyrrolo[1,2‐<i>a</i>]indol‐3‐ones

Abstract Herein, we present a novel and highly efficient strategy for the synthesis of synthetically valuable 3 H ‐pyrrolo[1,2‐ a ]indol‐3‐ones via a Rh(III)‐catalyzed regioselective [3+2] annulation strategy. The protocol ensures precise regioselective insertion of substituted 1,3‐enynes at the less sterically hindered site, while offering a broad substrate scope, excellent functional group compatibility, and mild reaction conditions. Moreover, the methodology is amenable to gram‐scale synthesis and demonstrates the successful application of terbinafine as a substrate within this transformation.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-03-11
DOI
https://doi.org/10.1002/ajoc.202400810
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Rh(III)‐Catalyzed Regioselective [3+2]‐Annulation of Indoles with 1,3‐Enynes to Access 3H‐pyrrolo[1,2‐a]indol‐3‐ones

Togati Naveen, Bhargav Desai, Pradeep Girase, Sanjeev Kumar et al.
Asian Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Rh(III)‐Catalyzed Regioselective [3+2]‐Annulation of Indoles with 1,3‐Enynes to Access 3H‐pyrrolo[1,2‐a]indol‐3‐ones

Togati Naveen, Bhargav Desai, Pradeep Girase, Sanjeev Kumar, Vinaykumar Kanchupalli, Sanjeev Jadhav
article en

Abstract

Abstract Herein, we present a novel and highly efficient strategy for the synthesis of synthetically valuable 3 H ‐pyrrolo[1,2‐ a ]indol‐3‐ones via a Rh(III)‐catalyzed regioselective [3+2] annulation strategy. The protocol ensures precise regioselective insertion of substituted 1,3‐enynes at the less sterically hindered site, while offering a broad substrate scope, excellent functional group compatibility, and mild reaction conditions. Moreover, the methodology is amenable to gram‐scale synthesis and demonstrates the successful application of terbinafine as a substrate within this transformation.

Asian Journal of Organic ChemistryVol. 14(5)
University of Hyderabad (IN), Sardar Vallabhbhai National Institute of Technology Surat (IN), National Institute of Pharmaceutical Education and Research - Ahmedabad (IN), National Institute of Pharmaceutical Education and Research (IN)
Openalex Percentile: Top 97%
Catalytic C–H Functionalization Methods
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