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Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes

Hong Hou, Yue Xu, Hai‐Bo Yang, Xiaoyun Chen, Chao‐Guo Yan, Yaocheng Shi, Shaoqun Zhu

2020Organic Letters58 citationsDOI

Abstract

Described herein is a visible-light mediated intermolecular radical cyclization approach to access heterocycles. Heteroatom radicals, such as silicon and phosphorus atom radicals, were generated via direct hydrogen atom abstraction by the photoexcited catalyst species with hydro-silanes and phosphine oxides. The radical addition/cyclization/HAT (hydrogen atom transfer) reaction sequences of 1,6-enynes and 1,6-dienes were highly efficient delivering the desired heterocycles in good yields.

Topics & Concepts

ChemistryRadicalSilanesHeteroatomHydrogen atom abstractionPhotochemistryHydrogen atomIntermolecular forceCatalysisPhosphineRadical cyclizationAtom (system on chip)Medicinal chemistryOrganic chemistryMoleculeAlkylSilaneEmbedded systemComputer scienceRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes | Litcius