Light-induced arylation (alkylation) of N-sulfonylhydrazones with boronic acids

Abstract

Di and triarylmethanes are an important class of compounds in many fields. Here, we report an efficient light-induced arylation (alkylation) for the synthesis of diarylmethanes, bis(diarylmethyl)benzenes, arylalkylmethanes, triarylmethanes from the...

Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base

“…Inspired by König’s work, we envisioned the use of boronic acids instead of aldehydes in pursuit of a photoactivated version of the Barluenga coupling that enables further functionalization of A . Notably, as we were completing these efforts, a parallel approach was reported by Plaza and Valdés. , This work (Scheme D) corroborates that effort, provides additional substrate examples, delineates the limits of the method’s effectiveness, and provides essential data from control experiments to understand the requirements of the photoactivation.…”

“…Notably, as we were completing these efforts, a parallel approach was reported by Plaza and Valdeś. 8,9 This work (Scheme 1D) corroborates that effort, provides additional substrate examples, delineates the limits of the method's effectiveness, and provides essential data from control experiments to understand the requirements of the photoactivation.…”

“…We note the correspondence of these results to published efforts. 8,9 It is also important to note that while neutral aromatic boronic acids were functional (see 3d), electron-deficient aryl boronic acids were not. Additionally, a functional group tolerance screen 14 showed that Lewis basic functionality had significant incompatibility with the reaction.…”

Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

“…Our idea is to avoid ex situ-generated diazo compounds, which are explosive and have issues with regard to storage and stability. We continue to be interested in the light-induced diazo-free generation of carbenes and the transformations of N -sulfonylhydrazones . We are interested in studying the chemistry of N -sulfonylhydrazones for the intramolecular cyclopropanation reaction in the presence of a base and light.…”