Strain-Release Functionalization of <i>N</i>-Aryl Bicyclo[1.1.0]butane Sulfonamides to Access Spirocyclic Sultams
Sultams are recognized as important scaffolds in drug discovery and medicinal chemistry. When integrated into spirocyclic structures, especially those containing cyclobutane units, they provide conformational rigidity and a well-defined three-dimensional structure, which enhances their physicochemical and pharmacokinetic properties. Despite their potential, the synthesis of spirocyclobutyl sultams has been scantly explored. In this study, we present a general strategy for synthesizing spirocyclobutyl benzosultams by combining the strain release of <i>N</i>-aryl bicyclo[1.1.0]butane sulfonamides with photoredox catalysis. This method enables the construction of a diverse library of functionalized spirocyclobutyl benzosultams by incorporation of a wide range of radicals, including SCF<sub>3</sub>, SCN, SO<sub>2</sub>R, and P(O)(OR)<sub>2</sub>.
Authors
- Durga Prasad Hari (ORCID: https://orcid.org/0000-0002-0734-8427)
- Manish Ranjan Sarkar (ORCID: https://orcid.org/0009-0006-9036-8256)
- Tushar Singha (ORCID: https://orcid.org/0000-0002-9424-6460)
- Subhayan Aich
Institutions
- Indian Institute of Science Bangalore (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-29
- DOI
- https://doi.org/10.1021/acs.orglett.5c03244
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Indian Institute of Science
- Department of Science and Technology, Ministry of Science and Technology, India
- University Grants Commission
- Ministry of Education, India
- Science and Engineering Research Board