Hydro-phosphorothiolation of Styrene and Cyclopropane with S-Hydrogen Phosphorothioates under Ambient Conditions.

ABSTRACT

A metal-free hexafluoroisopropanol-mediated hydro-phosphorothiolation of styrenes and donor-acceptor cyclopropanes with S-hydrogen phosphorothioates in a Markovnikov fashion has been developed under ambient reaction conditions to afford a library of S-alkyl phosphorothioates. Notably, this strategy provides a simple and efficient way to produce biologically significant kitazin and iprobenfos derivatives. Mechanistic studies disclose that the reaction proceeds through a carbocation intermediate.