The borrowing hydrogen (BH) principle, also called hydrogen auto-transfer, is a powerful approach which combines transfer hydrogenation (avoiding the direct use of molecular hydrogen) with one or more intermediate reactions to synthesize more complex molecules without the need for tedious separation or isolation processes. The strategy which usually relies on three steps, (i) dehydrogenation, (ii) intermediate reaction, and (iii) hydrogenation, is an excellent and well-recognized process from the synthetic, economic, and environmental point of view. In this context, the objective of the present review is to give a global overview on the topic starting from those contributions published prior to the emergence of the BH concept to the most recent and current research under the term of BH catalysis. Two main subareas of the topic (homogeneous and heterogeneous catalysis) have been identified, from which three subheadings based on the source of the electrophile (alkanes, alcohols, and amines) have been consid...

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Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Transition-metal-catalyzed C-alkylation of ketones and secondary alcohols, with alcohols, avoids use of organometallic or environmentally unfriendly alkylating agents by means of borrowing hydrogen (BH) or hydrogen autotransfer (HA) activation of the alcohol substrates. Water is formed as the only by-product, thus making the BH process atom-economical and environmentally benign. Diverse homogeneous and heterogeneous transition-metal catalysts, ketones, and alcohols can be used for this transformation, thus rendering the BH process promising for replacing those procedures that use traditional alkylating agents. This Minireview summarizes the advances during the last five years in transition-metal-catalyzed BH α-alkylation of ketones, and β-alkylation of secondary alcohols with alcohols. A discussion on the application of the BH strategy for C-C bond formation is included.

C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation.

This paper summarizes recent advances in α-alkylation reactions based on hydrogen borrowing methodologies using alcohol as an alkylating agent. This review provides a summary of recent progress toward the α-alkylation of carbonyl substrates, as well as relatively unactivated substrates bearing fewer acidic α-hydrogens, such as acetonitriles, acetamides, esters, methylpyrimidines, and methylquinolines. A summary of recent improvements in α-methylation strategies based on hydrogen borrowing methodologies has also been provided. Particular emphasis has been placed on highly practical and green chemistry approaches involving modified catalytic systems, including metal-supported heterogeneous catalysts and nanoparticle-based catalysts, as well as reactions conducted in the absence of a transition-metal catalyst. A review of recent achievements in methylation strategies using methanol as a methyl source, and their application to the α-methylation of ketones using transition-metal catalyzed hydrogen borrowing me...

Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies

Over the past few years, iridium complexes have been widely used in the direct functionalization of unactivated bonds. In the presence of iridium catalysts, inactive C–H and N–H bonds have been transformed into C–C and N–C bonds in dehydrative alkylation using alcohols, allylation using allyl carbonates, and alkylation using alkenes. Enantioselective variants of some reactions have also been reported.

Recent Advances in Iridium-Catalyzed Alkylation of C–H and N–H Bonds

A general and benign iron-catalyzed α-alkylation reaction of ketones with primary alcohols has been developed. The key to success of the reaction is the use of a Knolker-type complex as catalyst (2 mol %) in the presence of Cs2 CO3 as base (10 mol %) under hydrogen-borrowing conditions. Using 2-aminobenzyl alcohol as alkylation reagent allows for the "green" synthesis of quinoline derivatives.

Iron‐Catalyzed α‐Alkylation of Ketones with Alcohols

Effective synthesis of 2,5-disubstituted tetrahydrofurans from glycerol by catalytic alkylation of ketones

The iridium-catalyzed α-alkylation of ketones (II) and (VI) followed by reduction and application of a Fe(III)-mediated deprotection/cyclization methodology affords an isomeric mixture of tetrahydrofurans (IV)/(V) and (VIII).

Effective Synthesis of 2,5-Disubstituted Tetrahydrofurans from Glycerol by Catalytic Alkylation of Ketones.

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Effective synthesis of 2,5-disubstituted tetrahydrofurans from glycerol by catalytic alkylation of ketones

Effective Synthesis of 2,5-Disubstituted Tetrahydrofurans from Glycerol by Catalytic Alkylation of Ketones.