Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes

Herein, we present a three-component reaction through Rh(III)-catalyzed strain release of bicyclo[1.1.0]butanes (BCBs) to synthesize substituted acrylamides. This protocol represents the first example of a nucleophilic attack on the Rh(V) nitrenoid complex generated by the coupling of phenoxyacetamides and strained BCBs. The reaction proceeds under mild conditions and demonstrates broad compatibility with various functional groups on both phenoxyacetamides and nucleophiles, affording valuable substituted acrylamides. Furthermore, the products can be further transformed into important building blocks for synthesis. Preliminary mechanistic studies support the proposed catalytic cycle.

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Publication Details

Journal
Organic Letters
Published
2025-09-12
DOI
https://doi.org/10.1021/acs.orglett.5c03345
Citations
3
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.81
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article

Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes

Ponneri C. Ravikumar, Suman Pradhan, Saista Afreen, Shubham Kumar Dhal
3 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.81
article

Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes

Ponneri C. Ravikumar, Suman Pradhan, Saista Afreen, Shubham Kumar Dhal
article en
3 citations

Abstract

Herein, we present a three-component reaction through Rh(III)-catalyzed strain release of bicyclo[1.1.0]butanes (BCBs) to synthesize substituted acrylamides. This protocol represents the first example of a nucleophilic attack on the Rh(V) nitrenoid complex generated by the coupling of phenoxyacetamides and strained BCBs. The reaction proceeds under mild conditions and demonstrates broad compatibility with various functional groups on both phenoxyacetamides and nucleophiles, affording valuable substituted acrylamides. Furthermore, the products can be further transformed into important building blocks for synthesis. Preliminary mechanistic studies support the proposed catalytic cycle.

Organic LettersVol. 27(38)
Indian Institute of Science Education and Research Kolkata (IN), National Institute of Science Education and Research (IN), Indian Institute of Science Education and Research Mohali (IN), Indian Institute of Science Education and Research, Bhopal (IN), Indian Institute of Science Education and Research Berhampur (IN), Indian Institute of Science Education and Research, Tirupati (IN)
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
2.81
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