General Anti-Markovnikov Hydrophosphinylation of Olefins Using Disulfide as the Photocatalyst and a Hydrogen Atom Shuttle
Guoxiang Zhang, Hui He, Xiaoxiao Chen, Shao‐Fei Ni, Rong Zeng
Abstract
The photoinduced radical-based hydrophosphinylation suffered from substrate scope limitation due to the highly electrophilic property of the P(O) radical. Herein, we report an efficient catalytic system for the intermolecular anti-Markovnikov hydrophosphinylation of olefins using disulfide as a photocatalyst and also a hydrogen atom shuttle. This metal-free, base-free, and redox-neutral condition allowed the alkenes with diverse electronic properties to proceed with the anti-Markovnikov P-H addition efficiently. A plausible mechanism involving the HAT process between ArS• and P(O)-H was proposed.
Topics & Concepts
Markovnikov's ruleChemistryPhotocatalysisCatalysisHydrogen atomElectrophilePhotochemistryCombinatorial chemistryIntermolecular forceRegioselectivityOrganic chemistryMoleculeAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions