202596-55-2

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 872-53-7 cyclopentanealdehyde 
• 286-20-4 cyclohexane-1,2-epoxide 
• 127208-26-8 cis-2-(3-butenyl)-3-(2-phenylethyl)oxirane 
• 33240-34-5 cyclopentylmagnesium bromide 
• 104-53-0 3-phenyl-propionaldehyde 
• 1556-18-9 cyclopentyl iodide 
• 52829-98-8 1-cyclopentylethan-1-ol 
• 100-51-6 benzyl alcohol 
• 127208-50-8 (5Z)-8-phenyl-1,5-octadiene 

Downstream Products

• 67281-41-8 1-cyclopentyl-3-phenylpropan-1-one 

Relevant academic research and scientific papers

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.

Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes

A mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides has been developed. The catalytic system features the use of a common Ni(ii) precatalyst and a readily available bioxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The use of 1,5-hexadiene as an additive is an important reaction parameter that provides significant benefits in yield optimizations. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species that undergoes formal oxidative addition to the alkyl bromideviaa reductive cross-coupling pathway.

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.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.

Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl.