Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes

• Published in: Organic & biomolecular chemistry Vol. 21; no. 25; pp. 5171 - 5175
• Main Authors: Zhan, Jun-Long, Wang, Bing-Jie, Wang, Chen-Xi, Zhao, Xin-Ming, Zhou, Sai-Nan, Dou, Zao-Zao, Yang, Xin-Xin, Zhu, Lin, Ren, Wei
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 28.06.2023; Royal Society of Chemistry
• Subjects: Alkenes; Catalysis; Chemical synthesis; Chemistry; Chemistry, Organic; Copper; Functional groups; Oxidation; Phosphorylation; Physical Sciences; Regioselectivity; Science & Technology; HYDROPHOSPHORYLATION; PHOSPHONATES; ACIDS; H-PHOSPHINE OXIDES; VINYLPHOSPHINE OXIDES; BONDS; 1,1-DIBROMO-1-ALKENES; TERMINAL ALKYNES; SELECTIVE SYNTHESIS; DIPHENYLPHOSPHINE OXIDE

An efficient, practical and regioselective synthesis of ( E )-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this metho...