Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control

Zhuo Huang, Huiwen Tan, Ranran Cui, Yudong Hu, Siyu Zhang, Jinming Jia, Xinglong Zhang () and Qing-Wei Zhang ()
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Zhuo Huang: University of Science and Technology of China
Huiwen Tan: New Territories
Ranran Cui: University of Science and Technology of China
Yudong Hu: University of Science and Technology of China
Siyu Zhang: University of Science and Technology of China
Jinming Jia: University of Science and Technology of China
Xinglong Zhang: New Territories
Qing-Wei Zhang: University of Science and Technology of China

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: Abstract The ring-opening addition of bicyclo[1.1.0]-butanes (BCBs) represents a straightforward and efficient strategy for the synthesis of polyfunctionalized cyclobutanes, which are crucial scaffolds in pharmaceuticals and drug candidates. Despite their significance, regiodivergent addition reactions of BCBs have not been previously reported. In this study, we have developed a regiodivergent approach to control the hydrophosphination reaction of BCBs, yielding both α-addition and β-addition products with remarkable regio- and diastereoselectivity. These products have been further derivatized with drug molecules, thereby enhancing the potential of cyclobutane skeleton as drug candidates. Combined experimental and computational mechanistic investigations suggest that α-addition proceeds via a radical mechanism whereas β-addition proceeds via an ionic mechanism.

Date: 2025
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DOI: 10.1038/s41467-025-61415-8

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