B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed [2π + 2σ] Cycloadditions of Carbodiimides with Bicyclo[1.1.0]butanes
Amidines are a privileged structural motif in a series of pharmaceuticals. In this work, we developed a simple, scalable, and transition-metal-free method for the efficient [2π + 2σ] cycloaddition of carbodiimides with bicyclo[1.1.0]butanes. The approach enabled the synthesis of 28 examples of functionalized amidines under mild reaction conditions in up to 99% yield with <i>Z</i>/<i>E</i> ratios of up to >19:1.
Authors
- Lei Xiao (ORCID: https://orcid.org/0000-0002-4135-5911)
- Douglas W. Stephan (ORCID: https://orcid.org/0000-0001-8140-8355)
- Jing Guo (ORCID: https://orcid.org/0000-0001-8710-4627)
- Yufen Zhao (ORCID: https://orcid.org/0000-0003-3560-435X)
- Li Lin (ORCID: https://orcid.org/0000-0001-5154-3804)
- Yalin Xiong (ORCID: https://orcid.org/0000-0003-1079-3860)
Institutions
- Ningbo University (CN)
- University of Toronto (CA)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-29
- DOI
- https://doi.org/10.1021/acs.orglett.5c01898
- Citations
- 4
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Natural Science Foundation of Ningbo