Litcius/Paper detail

Photocatalytic Alkylation of C(sp <sup>3</sup> )−H Bonds Using Sulfonylhydrazones**

Antonio Pulcinella, Stefano Bonciolini, Florian Lukas, Andrea Sorato, Timothy Noël

2022Angewandte Chemie International Edition49 citationsDOIOpen Access PDF

Abstract

Abstract The ability to construct C(sp 3 )−C(sp 3 ) bonds from easily accessible reagents is a crucial, yet challenging endeavor for synthetic organic chemists. Herein, we report the realization of such a cross‐coupling reaction, which combines N‐ sulfonyl hydrazones and C(sp 3 )−H donors through a diarylketone‐enabled photocatalytic hydrogen atom transfer and a subsequent fragmentation of the obtained alkylated hydrazide. This mild and metal‐free protocol was employed to prepare a wide array of alkyl‐alkyl cross‐coupled products and is tolerant of a variety of functional groups. The application of this chemistry further provides a preparatively useful route to various medicinally‐relevant compounds, such as homobenzylic ethers, aryl ethyl amines, β‐amino acids and other moieties which are commonly encountered in approved pharmaceuticals, agrochemicals and natural products.

Topics & Concepts

SulfonylAlkylationAlkylChemistryArylCombinatorial chemistryPhotocatalysisReagentOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques