125153-19-7

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 100-42-5 styrene 
• 3277-89-2 phenethylmagnesium bromide 
• 104-53-0 3-phenyl-propionaldehyde 
• 626-62-0 Cyclohexyl iodide 
• 60-12-8 2-phenylethanol 
• 1193-81-3 rac-1-cyclohexylethanol 
• 823-76-7 Cyclohexyl methyl ketone 
• 90878-19-6 phenethylmagnesium chloride 
• 100-49-2 cyclohexylmethyl alcohol 
• 100-51-6 benzyl alcohol 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 43125-06-0 1-cyclohexyl-3-phenyl-1-propanone 
• 154777-27-2 1-cyclohexyl-3-phenyl-1-propyl phenyl sulfide 
• 154777-51-2 1-cyclohexyl-1-mesyl-3-phenylpropane 

Relevant academic research and scientific papers

Cross-coupling reaction of alcohols for carbon-carbon bond formation using pincer-type NHC/palladium catalysts

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H2 gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high alcohol product selectivity. The Royal Society of Chemistry 2010.

Selective C-alkylation Between Alcohols Catalyzed by N-Heterocyclic Carbene Molybdenum

The first implementation of a molybdenum complex with an easily accessible bis-N-heterocyclic carbene ligand to catalyze β-alkylation of secondary alcohols via borrowing-hydrogen (BH) strategy using alcohols as alkylating agents is reported. Remarkably high activity, excellent selectivity, and broad substrate scope compatibility with advantages of catalyst usage low to 0.5 mol%, a catalytic amount of NaOH as the base, and H2O as the by-product are demonstrated in this green and step-economical protocol. Mechanistic studies indicate a plausible outer-sphere mechanism in which the alcohol dehydrogenation is the rate-determining step.

Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Room-Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity

We report herein an unprecedented highly efficient Guerbet-type reaction at room temperature (catalytic TON up to >6000). This β-alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher-order secondary alcohols in an economical, redox-neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee. In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.

Copper-Catalyzed and Indium-Mediated Methoxycarbonylation of Unactivated Alkyl Iodides with Balloon CO

This work emphasizes the synthesis of alkyl esters via Cu-catalyzed and In-mediated alkoxycarbonylation of unactivated alkyl iodides in the presence of In or InI. The reactions were suitable for the preparation of primary, secondary, and even tertiary alkyl esters, representing an exceptionally rare example for the creation of quaternary carbon centers upon formation of esters. The preliminary mechanistic studies indicated that alkyl radicals were involved, and Cu/In/CO played a cooperative role in the carbonylation event.

C-Alkylation of Secondary Alcohols by Primary Alcohols through Manganese-Catalyzed Double Hydrogen Autotransfer

A new Mn-catalyzed alkylation of secondary alcohols with non-activated alcohols is presented. The use of a stable and well-defined manganese pincer complex, stabilized by a PNN ligand, together with a catalytic amount of base enabled the conversion of renewable alcohol feedstocks to a broad range of higher-value alcohols in good yields with water as the sole byproduct. The strategy eliminates the need for exogenous and detrimental alkyl halides as well as the use of noble metal catalysts, making the C-alkylation through double hydrogen autotransfer a highly sustainable and environmentally benign process. Mechanistic investigations support a hydrogen autotransfer mechanism in which a non-innocent ligand plays a crucial role.

Regioselective Hydrohydroxyalkylation of Styrene with Primary Alcohols or Aldehydes via Ruthenium-Catalyzed C?C Bond Forming Transfer Hydrogenation

Transfer hydrogenative coupling of styrene with primary alcohols using the precatalyst HClRu(CO)(PCy3)2modified by AgOTf or HBF4delivers branched or linear adducts from benzylic or aliphatic alcohols, respectively. Related

CuI/H2/NaOH-catalyzed cross-coupling of two different alcohols for carbon-carbon bond formation: "Borrowing hydrogen"?

Not borrowed: A new method was developed for the cross-coupling of two different alcohols (see scheme). This carbon-carbon bond formation was realized by using a small amount of CuBr (0.05-0.2 mol %) and NaOH (4-20 mol %) in the presence of H2 (1 atm), and provides an alternative procedure for longer-chain alcohols. The catalytic cycle was different from those reported to date for the Guerbet reaction involving "borrowing hydrogen". Copyright

Indium-copper and indium-silver mediated Barbier-Grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

(Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I2 or In/AgI/I2 system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I 2 were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

Generation of Aminyl Radicals using Sulfenamides as Synthetic Precursors

Sulfenamides are synthesised from reaction between amines and N-(benzenesulfenil)-phthalimide or benzenesulfenyl chloride.The sulfenamides undergo reaction with tributyltin hydride to yield aminyl radicals which can be cyclised onto suitable alkenes. Key Words: sulfenamides; aminyl radicals; tributyltin hydride; radical-cyclisation; N-(benzenesulfenyl)phthalimide