Stereo- and Regioselective <i>cis</i>-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>
Hong Hou, Bing Zhou, Jiawei Wang, Dengyang Zhao, Duhao Sun, Xiao Yun Chen, Ying Han, Chao‐Guo Yan, Yaocheng Shi, Shaoqun Zhu
Abstract
Described herein is a stereo- and regioselective cis -hydrophosphorylation reaction of the internal alkyne of 1,3-enynes that accesses various 1,3-dienes in good isolated yields. The visible-light irradiation of NiCl 2 (PPh 3 ) 2 allows the generation of highly reactive nickel(II)-phosphorus species that subsequently migrate into the internal alkyne of the 1,3-enynes and protonate the resulting vinyl nickel species, leading to various phosphinoyl 1,3-butadienes under mild reaction conditions.
Topics & Concepts
RegioselectivityAlkyneChemistryIrradiationNickelVisible spectrumPhotochemistryCatalysisOrganic chemistryOptoelectronicsPhysicsNuclear physicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods