Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes
Shubham K Dhal1,2, Saista Afreen1,2, Sikun Pradhan2
1Department of Chemistry, Indian Institute of Science Education and Research (IISER), Tirupati, Andhra Pradesh 517619, India.
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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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