C-Alkylation by Hydrogen Autotransfer Reactions

Abstract

The development of practical, efficient, and atom-economical methods for the formation of carbon–carbon bonds remains a topic of considerable interest in current synthetic organic chemistry. In this review, we have summarized selected topics from the recent literature with particular emphasis on C-alkylation processes involving hydrogen transfer using alcohols as alkylation reagents. This review includes selected highlights concerning recent progress towards the modification of catalytic systems for the α-alkylation of ketones, nitriles, and esters. Furthermore, we have devoted a significant portion of this review to the methylation of ketones, alcohols, and indoles using methanol. Lastly, we have also documented recent advances in β-alkylation methods involving the dimerization of alcohols (Guerbet reaction), as well as new developments in C-alkylation methods based on sp ³ C–H activation.

This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J.Ramón.