Photodecarboxylative Radical Cascade Involving <i>N</i>-(Acyloxy)phthalimides for the Synthesis of Pyrazolones

Abstract

We disclose N ′-arylidene- N -acryloyltosylhydrazides as novel skeletons for the synthesis of biologically relevant alkylated pyrazolones through a photoinduced radical cascade with N -(acyloxy)pthalimides as readily available alkyl surrogates. The reaction proceeds through the formation of a photoactivated electron donor–acceptor (EDA) complex between alkyl N -(acyloxy)phthalimide (NHPI) esters and LiI/PPh 3 as a commercially available donor system. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated alkylated pyrazolones under mild and transition-metal-free conditions.

Topics & Concepts