Base-Promoted Ring Opening of Bicyclo[1.1.0]butanes for Diastereoselective Hydroalkynylthiolation
Abstract Herein, we disclose a transition-metal-free base-promoted syn-selective hydroalkynylthiolation of bicyclo[1.1.0]butanes (BCBs) under mild conditions. The reaction involves the in situ formation of the alkylnylthiolate anion from readily available 1,2,3-thiadiazoles in the presence of a base, which adds to bicyclo[1.1.0]butanes (BCBs) to release the strain. The broad substrate scope, good functional group compatibility, applicability in late-stage derivatization of bioactive molecules, downstream product transformations, and scale-up synthesis demonstrate the synthetic potential of the present method.
Authors
- Ravi Kumar (ORCID: https://orcid.org/0000-0001-8149-6498)
- Aaron Taites (ORCID: https://orcid.org/0009-0003-2606-5021)
- Kiran
- Sujoy Saha (ORCID: https://orcid.org/0009-0000-6273-0082)
Institutions
- National Institute of Pharmaceutical Education and Research (IN)
- National Institute of Pharmaceutical Education and Research (IN)
- National Institute of Pharmaceutical Education and Research (IN)
- National Institute of Pharmaceutical Education and Research (IN)
- National Institute of Pharmaceutical Education and Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c04092
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, India