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September 16, 20255 citations

Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo1.1.0butanes.

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SDShubham Kumar DhalSASaista AfreenSPSuman Pradhan

Key Points

  • The reaction efficiently yields valuable substituted acrylamides under mild conditions, showcasing broad compatibility with various groups.
  • Notably, it represents the first nucleophilic attack on the Rh(V) nitrenoid complex derived from phenoxyacetamides and bicyclo[1.1.0]butanes.
  • Mechanistic studies indicate a well-defined catalytic cycle, providing insights into the reaction complexities involved.
  • These products can serve as critical building blocks for further synthetic applications in organic chemistry.

Abstract

Herein, we present a three-component reaction through Rh(III)-catalyzed strain release of bicyclo1.1.0butanes (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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Cite This Study

Dhal et al. (2025) studied this question.

synapsesocial.com/papers/68c93fe601120bef803bae8ahttps://doi.org/10.1021/acs.orglett.5c03345
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