Tf2O/DMSO-mediated dual activation of aryl phosphinate to access various aryl phosphonates

Hui-Qi Yue; Da-Wei Shi; Ming Li; Si-Qi Gao; Mu-Xin Sun; Shun Zhang; Shang-Dong Yang; Bin Yang

doi:10.1039/d3cc03250g

Tf₂O/DMSO-mediated dual activation of aryl phosphinate to access various aryl phosphonates

Chem Commun (Camb). 2023 Sep 7;59(72):10817-10820. doi: 10.1039/d3cc03250g.

Authors

Hui-Qi Yue¹, Da-Wei Shi¹, Ming Li¹, Si-Qi Gao¹, Mu-Xin Sun¹, Shun Zhang¹, Shang-Dong Yang², Bin Yang¹

Affiliations

¹ College of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, People's Republic of China. yangbin_hy@ytu.edu.cn.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

PMID: 37602683
DOI: 10.1039/d3cc03250g

Abstract

A metal-free method for the dual activation of aryl phosphinate has been developed; the P-H and P-O bonds are sequentially activated by the Tf₂O/DMSO system. Without the requirement of metals and unstable P-reagents, this one-pot procedure provides a convenient and practical access to a variety of aryl phosphonates. A mechanism involving twice generation of electrophilic P-species and two S_N-processes is proposed on the basis of the control experiments.