57013-04-4

Upstream product

• 1088-01-3 tricyclohexylborane 
• 59648-89-4 1,2-dimethoxyethenyllithium 
• 119-60-8 dicyclohexyl ketone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 823-76-7 Cyclohexyl methyl ketone 
• 53317-13-8 1,1-dicyclohexylethanol 
• 931-50-0 cyclohexylmagnesium bromide 

Downstream Products

• 1356012-67-3 1,1-dibromo-2,2-dicyclohexylcyclopropane 
• 1356012-23-1 C₂₃H₃₁N 
• 1356012-53-7 3,3'-(3,3-dicyclohexylprop-2-ene-1,1-diyl)bis(1H-indole) 
• 1356012-54-8 3,3'-((3,3-dicyclohexyloxiran-2-yl)methylene)bis(1H-indole) 
• 1356012-49-1 3,3'-(3,3-dicyclohexylprop-2-ene-1,1-diyl)bis(5-methoxy-1H-indole) 
• 1356012-51-5 3,3'-((3,3-dicyclohexyloxiran-2-yl)methylene)bis(5-methoxy-1H-indole) 
• 1356012-55-9 3,3'-(3,3-dicyclohexylprop-2-ene-1,1-diyl)bis(5-fluoro-1H-indole) 
• 1356012-56-0 3,3'-((3,3-dicyclohexyloxiran-2-yl)methylene)bis(5-fluoro-1H-indole) 
• 1356012-43-5 3-(3,3-dicyclohexylallyl)-5-methoxy-1H-indole 
• 1356012-69-5 1-bromo-2,2-dicyclohexylcyclopropane 
• 1356012-59-3 cycloprop-2-ene-1,1-diyldicyclohexane 
• 2319-61-1 1,1-dicyclohexylethane 

Relevant academic research and scientific papers

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions

A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.

Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols

We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis. The use of fac-[Ir(ppy)3] (ppy=2-pyridylphenyl) photocatalyst and shelf-stable Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, as a CF2H source is the key to success. The well-designed photoredox system achieves synthesis of not only β-CF2H-substituted alcohols but also ethers and an ester from alkenes through solvolytic processes. The present method allows a single-step and regioselective formation of C(sp3)-CF2H and C(sp3)-O bonds from C=C moiety in alkenes, such as hydroxydifluoromethylation, regardless of terminal or internal alkenes. Moreover, this methodology tolerates a variety of functional groups. Light up the bulb! A novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis has been developed (see scheme). An Ir photocatalyst is useful for the generation of a CF2H radical through one-electron reduction of Hu's reagent. The present reaction system produces not only various β-CF2H-substituted alcohols, but also ethers and esters in regiospecific manners under mild conditions.

Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides

(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.

Divergent outcomes of gold(I)-catalyzed indole additions to 3,3-disubstituted cyclopropenes

Depending on the conditions employed, gold(I)-catalyzed addition of indoles to 3,3-disubstituted cyclopropenes can be controlled to yield either 3-(E)-vinylindoles (3) or bis-indolylalkanes (4). If the cyclopropene substituents are sterically bulky, unprecedented gold-catalyzed oxidation under air occurs to yield bis-indolylalkene (5) and epoxide (6) at room temperature.

A CONVENIENT ROUTE TO SYMMETRIC 1,1-DIALKYLETHENES FROM 1,2-DIMETHOXYETHENYLLITHIUM AND TRIALKYLBORANES

1,1-Dialkylethenes are prepared from 1,2-dimethoxyethenyllithium and organoboranes by treatment with trichloroacetic acid and then with sodium acetate-acetic anhydride and TiCl4/Ti(OPri)4.