95465-73-9

Upstream product

• 621-16-9 1-phenyl-3-<(3-trifluoromethyl)phenyl>-2-propen-1-one 
• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 98-85-1 1-Phenylethanol 
• 98-86-2 acetophenone 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 

Relevant academic research and scientific papers

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols

A homogeneous cobalt-catalyzed β-alkylation of secondary alcohols with primary alcohols to selectively synthesize ketones via acceptorless dehydrogenative coupling is reported for the first time. Notably, this transformation is environmentally benign and atom economical with water and hydrogen gas as the only byproducts.

Nonbifunctional Outer-Sphere Strategy Achieved Highly Active α-Alkylation of Ketones with Alcohols by N-Heterocyclic Carbene Manganese (NHC-Mn)

The unusual nonbifunctional outer-sphere strategy was successfully utilized in developing an easily accessible N-heterocyclic carbene manganese (NHC-Mn) system for highly active α-alkylation of ketones with alcohols. This system was efficient for a wide range of ketones and alcohols under mild reaction conditions, and also for the green synthesis of quinoline derivatives. The direct outer-sphere mechanism and the high activity of the present system demonstrate the potential of nonbifunctional outer-sphere strategy in catalyst design for acceptorless dehydrogenative transformations.

NNN pincer Ru(II)-complex-catalyzed α-alkylation of ketones with alcohols

A series of novel ruthenium(II) complexes supported by a symmetrical NNN ligand were prepared and fully characterized. These complexes exhibited good performance in transfer hydrogenation to form new C-C bonds using alcohols as the alkylating agents, generating water as the only byproduct. A broad range of substrates, including (hetero)aryl- or alkyl-ketones and alcohols, were well tolerated under the optimized conditions. Notably, α-substituted methylene ketones were also investigated, which afforded α-branched steric hindrance products. A potential application of α-alkylation of methylene acetone to synthesize donepezil was demonstrated, which provided the desired product in 83% yield. Finally, this catalytic system could be applied to a one-pot double alkylation procedure with sequential addition of two different alcohols. The current protocol is featured with several characteristics, including a broad substrate scope, low catalyst (0.50 mol %) loadings, and environmental benignity.

Use of a Cyclometalated Iridium(III) Complex Containing a N∧C∧N-Coordinating Terdentate Ligand as a Catalyst for the α-Alkylation of Ketones and N-Alkylation of Amines with Alcohols

A cyclometalated iridium(III) complex containing a N∧C∧N-coordinating terdentate ligand [Ir(dpyx-N,C,N)Cl(μ-Cl)]2 was found to be a general and highly effective catalyst for the α-alkylation of ketones and N-alkylation of amines with alcohols. In the presence of catalyst (1 mol % Ir) and base (0.2-0.5 equiv), a variety of desirable products were obtained in good yields under an air atmosphere. Notably, this research exhibited the new potential of Ir(III) complexes bearing non-Cp? ligand and will facilitate the progress of the hydrogen autotransfer process.

A base-controlled chemoselective transfer hydrogenation of α,β-unsaturated ketones catalyzed by [IrCpCl2]2 with 2-propanol

A simple homogeneous catalyst system based on commercially available [IrCpCl2]2 has been developed for the conjugate reduction of α,β-unsaturated ketones. Under the optimized conditions, a wide range of α,β-unsaturated ketones were reduced to saturated ketones in 83-98% yield. While switching the base from K2CO3 to KOH, saturated alcohols was selectively obtained.

RuHCl(CO)(PPh3)3-catalyzed R-alkylation of ketones with primary alcohols

The α-alkylation reaction of ketones with primary alcohols to give α-alkylated ketones was achieved using RuHCl(CO)(PPh3) 3 as a catalyst in the presence of Cs2CO3 as a base. This reaction proceeds via an aldol condensation of ketones with aldehydes, formed via transfer dehydrogenation of alcohols, to give α,β-unsaturated ketones, which then undergo transfer hydrogenation with primary alcohols to give R-alkylated ketones and aldehydes, the latter of which participate in the next catalytic cycle. While the reaction of aliphatic primary alcohols was sluggish compared with that of benzylic alcohols, a catalytic amount of 1,10-phenanthroline was found to promote the alkylation dramatically.