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.
Authors
- Ponneri C. Ravikumar (ORCID: https://orcid.org/0000-0002-5264-820X)
- Suman Pradhan (ORCID: https://orcid.org/0000-0002-5942-3206)
- Saista Afreen (ORCID: https://orcid.org/0000-0001-6629-8362)
- Shubham Kumar Dhal
Institutions
- 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)
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