Ruthenium-catalyzed β-alkylation of secondary alcohols with primary alcohols

Bai, Wei; Jia, Guochen

doi:10.1016/j.ica.2015.03.023

Cited by 27 publications

(8 citation statements)

References 94 publications

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“…Other alternatives concerning the use of alcohols as starting reagents in BH processes involve the use of primary and secondary alcohols to yield the corresponding β-alkylated products (Figure ). As in the previous case, ruthenium and iridium catalysts have been again extensively applied in these BH processes. − For example, a ruthenium compound containing a triazoledicarbene ligand was prepared and characterized as a tetraruthenium species 25 showing an excellent catalytic activity in the β-alkylation of secondary alcohols with primary alcohols (Scheme ). …”

Section: Borrowing Hydrogen Methodology In Homogeneous Catalysismentioning

confidence: 99%

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

2018

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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 considered. Then the type of bond being formed (carbon-carbon and carbon heteroatom) has been taken into account to end-up with the intermediate reaction working in tandem with the metal-catalyzed hydrogenation/dehydrogenation step. The review has been completed with the more recent advances in asymmetric catalysis using the BH strategy.

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Section: Borrowing Hydrogen Methodology In Homogeneous Catalysismentioning

confidence: 99%

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

2018

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“…Several examples of non‐deoxygenative cross‐alkylation of alcohols are known, primarily involving ruthenium catalysis. For example, Cho and Shim, Ramón and Yus, Peris, Lau, Crabtree, Jia and Kundu and co‐workers have reported the beta‐alkylation of secondary alcohols with primary alcohols to generate the Guerbet products in good yields, and Beller and co‐workers reported the methylation of 2‐arylethanols with methanol. Madsen and Achard reported the alkylation of secondary alcohols to form ketones.…”

Section: Methodsmentioning

confidence: 99%

Ru‐Catalyzed Completely Deoxygenative Coupling of 2‐Arylethanols through Base‐Induced Net Decarbonylation

Manojveer

Forrest

Johnson

2018

Chemistry A European J

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Substituted arylethanols can be coupled by using a readily available Ru catalyst in a fully deoxygenative manner to produce hydrocarbon chains in one step. Control experiments indicate that the first deoxygenation occurs through an aldol condensation, whereas the second occurs through a base-induced net decarbonylation. This double deoxygenation enables further development in the use of alcohols as versatile and green alkylating reagents, as well as in other fields, such as deoxygenation and upgrading of overfunctionalized biomass to produce hydrocarbons.

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“…(7)]. The ruthenium complex [RuCl 2 (PPh 3 ) 2 (2‐aminomethylpyridine)] effectively catalyzes the β‐alkylation of both aryl‐ and alkyl‐substituted secondary alcohols with benzylic and alkyl alcohols . In the presence of external dihydrogen, the minor alkylated ketone species can be reduced to the corresponding alkylated alcohol [Eq.…”

Section: Transition‐metal‐catalyzed C‐alkylation Of Ketones and Secomentioning

confidence: 99%

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

2015

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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.

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Ruthenium-catalyzed β-alkylation of secondary alcohols with primary alcohols

Cited by 27 publications

References 94 publications

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Ru‐Catalyzed Completely Deoxygenative Coupling of 2‐Arylethanols through Base‐Induced Net Decarbonylation

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

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