Nickel‐catalyzed α‐alkylation of ketones with benzyl alcohols

Wu, Di; Wang, Yubin; Li, Min; Shi, Lei; Liu, Jichang; Liu, Ning

doi:10.1002/aoc.6493

Cited by 15 publications

(1 citation statement)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Related Knölker-type catalysts were utilized in these transformations. Other disclosures of base-metal-catalyzed deoxygenative functionalization of alcohols have been made employing iron − cobalt, − and nickel. − …”

Section: Deoxygenative Functionalizationmentioning

confidence: 99%

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Cook,

Newman

2024

Chem. Rev.

View full text Add to dashboard Cite

Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods for their functionalization require them to first be converted into a more activated derivative, while recent years have seen a vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can be used toward this goal. These transformations are broadly classified into three categories. Deoxygenative functionalizations, representing derivatization of the C−O bond, enable the alcohol to act as a leaving group toward the formation of new C−C bonds. Etherifications, characterized by derivatization of the O−H bond, represent classical reactivity that has been modernized to include mild reaction conditions, diverse reaction partners, and high selectivities. Lastly, chain functionalization reactions are described, wherein the alcohol group acts as a mediator in formal C−H functionalization reactions of the alkyl backbone. Each of these three classes of transformation will be discussed in context of intermolecular arylation, alkylation, and related reactions, illustrating how catalysis can enable alcohols to be directly harnessed for organic synthesis.

show abstract

Section: Deoxygenative Functionalizationmentioning

confidence: 99%

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Cook,

Newman

2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

Well‐Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α‐Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines

et al. 2022

View full text Add to dashboard Cite

The "borrowing hydrogen" (BH) method for C-alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst for borrowing hydrogen transformation is a key challenge to be witnessed. Herein we have presented a synthesis of non-phosphine, easily accessible and bench stable SNSÀ Ni complexes. The Ni-catalyst was successfully applied for the C-alkylation of ketone enolates to α-alkylated ketones. Primary alcohol with different functional groups and various heteroaromatic alcohols are well tolerated. The present catalyst system was efficiently applied to gram scale synthesis and also the green chemistry metrics of the reaction were calculated. The present protocol was also extended successfully for the synthesis of biologically important quinoline moieties. Finally, various control experiments and deuterium labelled experiments suggest that the reaction proceeds via borrowing hydrogen pathway.

show abstract

Recent Advances for Alkylation of Ketones and Secondary Alcohols Using Alcohols in Homogeneous Catalysis

2022

View full text Add to dashboard Cite

The alkylation of ketones or secondary alcohols using alcohols as alkylating agents via hydrogen borrowing strategy presents a powerful method for the synthesis of �-alkylated ketones. In this review, we summarize the progress catalyzed by Ir, Pd, Rh, Ru, Mn, Fe, Co, Ni, and Cu catalysts for the α-alkylation of ketones with alcohols and crosscoupling of secondary alcohols with alcohols from 2017 to 2021. A wide range of ketones (aromatic and aliphatic ketones) and alcohols (benzylic and aliphatic primary alcohols, aromatic and aliphatic secondary alcohols, alkenyl alcohols, and diols) are well tolerated. Furthermore, we also discuss current challenges and propose perspectives on the coming development in this filed. The objective of the present review is to give an overview on recent advances for α-alkylation of ketones with alcohols and β-alkylation of secondary alcohols with alcohols. Finally, we hope that this review will give inspirations on alkylation of ketones or secondary alcohols with alcohols.

show abstract

Nickel‐catalyzed α‐alkylation of ketones with benzyl alcohols

Cited by 15 publications

References 39 publications

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Well‐Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α‐Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines

Recent Advances for Alkylation of Ketones and Secondary Alcohols Using Alcohols in Homogeneous Catalysis

Contact Info

Product

Resources

About