Liu Bo, Li Jianji, Hu Yifan, Chen Qian, Liu Yan, Ji Shaomin, Maruoka Keiji, Huo Yanping, Zhang Hao-Li
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, P. R. China.
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
J Org Chem. 2022 Aug 19;87(16):11281-11291. doi: 10.1021/acs.joc.2c01502. Epub 2022 Aug 5.
A photocatalyst- and additive-free visible-light-induced α-C(sp)-H phosphinylation of unactivated ethers involving a C-O bond cleavage with molecular oxygen as the sole oxidant at room temperature has been achieved. This method provides a sustainable access to α-hydroxyphosphine oxides in up to 88% yield with good functional group compatibility under mild and neutral conditions (34 examples). Moreover, the subsequent two-step conversion of the resulting dihydroxy diarylphosphine oxides afforded α-phosphinylated cyclic ethers in good overall yields (10 examples).
