Nickel-Catalyzed Radical Ring-Opening Phosphorylation of Cycloalkyl Hydroperoxides Leading to Distal Acylphosphine Oxides

Yue Ying; Ziyi Ye; An Wang; Xingjie Chen; Shanshan Meng; Pengxiang Xu; Yuxing Gao; Yufen Zhao

doi:10.1021/acs.orglett.2c04233

Nickel-Catalyzed Radical Ring-Opening Phosphorylation of Cycloalkyl Hydroperoxides Leading to Distal Acylphosphine Oxides

Org Lett. 2023 Feb 17;25(6):928-932. doi: 10.1021/acs.orglett.2c04233. Epub 2023 Feb 2.

Authors

Yue Ying¹, Ziyi Ye¹, An Wang¹, Xingjie Chen¹, Shanshan Meng², Pengxiang Xu¹, Yuxing Gao¹, Yufen Zhao³

Affiliations

¹ Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China.
² State Key Laboratory of Molecular Vaccinology and Molecular Diagnostics and Center for Molecular Imaging and Translational Medicine, School of Public Health, Xiamen University, Xiamen 361102, Fujian, China.
³ Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China.

PMID: 36729387
DOI: 10.1021/acs.orglett.2c04233

Abstract

A facile and efficient nickel-catalyzed C-C bond cleavage/phosphorylation of various cycloalkyl hydroperoxides was developed. This radical ring-opening strategy provided practical access to structurally diverse distal ketophosphine oxides in one pot through concurrent C═O/C-P bond formation with high atom economy under mild room temperature and base-free conditions.