Recent Advances in Catalytic C(sp2)–H Allylation Reactions

Citations Over TimeTop 1% of 2017 papers

Abstract

The linear or branched allyl moieties on aromatic rings are well-known as ubiquitous structural motifs found in a range of natural products and medicinally relevant molecules. They also represent an important class of organic intermediates for the transformation of an olefin group into many useful functional groups. Established methods for the installation of allylic groups rely primarily on nucleophilic substitution or transmetalation of aryl metal complexes to allyl electrophiles, Lewis acid-mediated Friedel–Crafts allylation of electron-rich arenes, and Tsuji–Trost allylation reactions with π-allyl species. Complementing previous protocols, the transition metal-catalyzed allylation reactions via C–H activation strategy using various allylic surrogates like allylic acetates, allylic carbonates, allylic phosphonates, allylic halides, allylic alcohols, vinyl oxiranes, allenes, 1,3-dienes, and others have recently emerged as a powerful tool for creating the corresponding allyl, crotyl and prenyl moieties. This review, which includes all reported methods in the literature until the beginning of 2017, focuses on recent progress on direct allylation reactions of aromatic and vinylic C(sp2)–H bonds with allylic sources and various transition metal catalysts.

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