92319-61-4

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 100-49-2 cyclohexylmethyl alcohol 
• 7647-01-0 hydrogenchloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 64-17-5 ethanol 
• 27819-71-2 2-chloro-3',4'-dimethoxybenzoin 
• 41841-04-7 2-(2-chlorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone 
• 144-79-6 chloromethyldiphenylsilane 
• 84072-32-2 1-[(Z)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 931-50-0 cyclohexylmagnesium bromide 
• 55409-09-1 1,2-dicyclohexyl-2-hydroxy-ethanone 
• 82303-13-7 (4-methoxyphenyl)zinc(II) bromide 

Downstream Products

• 107210-54-8 4,5-Dicyclohexyl-2-((E)-propenyl)-[1,3]dioxolane 
• 55409-09-1 1,2-dicyclohexyl-2-hydroxy-ethanone 
• 107210-59-3 1,2-Dicyclohexyl-2-((E)-3-phenyl-but-1-enyloxy)-ethanol 
• 393166-59-1 [R-(4α,5β)]-4,5-dicyclohexyl-2-[(triphenylmethoxy)methyl]-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

4,5-Dicyclohexyl-1,3,2-dioxathiolane 2-Oxide, C14H24O3S

The title compound, 4,5-dicyclohexyl-1,3,2-dioxathiolane 2-oxide (1), adopts a half-chair (envelope) conformation with the S=O bond taking up a pseudo-axial position.The cyclohexyl groups occupy trans positions.

Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species

Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species.

Synthesis method of aliphatic pinacol

The invention provides a synthesis method of aliphatic pinacol, the reaction condition is mild, the reaction yield is high, the reaction time is short, and the technical scheme is as follows: in an anhydrous tetrahydrofuran solvent, through the interactio

Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes to Form Hindered Secondary Alcohols

Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).

Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME

The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields.

Mechanistic study of half-titanocene-based reductive pinacol coupling reaction

The reductive pinacol coupling reaction of aldehydes or ketones creating a new C-C bond has been a major tool to produce 1,2-diol compounds. The reaction mechanism is known to be composed of sequential three steps (activation, coupling, and dissociation). In this work, we studied the dissociation step of half-titanocene-based catalytic systems. Cp and Cp* derivatives of the pinacolato-bridged dinuclear complex were synthesized and evaluated as possible models for intermediates from the coupling step. We monitored 1H-NMR spectra of the reaction between the metalla-pinacol intermediates and D2O. New reaction routes of the dissociation step including oxo- and pinacolato-dibridged dinuclear complexes and oxo-bridged multinuclear complexes have been suggested. Copyright

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

Reductive self-coupling reaction of imines and aldehydes induced by strontium metal

Aromatic aldimines reacted with Sr in the presence of a catalytic amount of iodine to give self-coupling products in good yields, whereas aromatic and aliphatic aldehydes underwent a similar reaction effected by the combined use of Sr and Al(OEt)3. Copyright

Light-fluorous TEMPO: reagent, spin trap and stable free radical

The synthesis of two light-fluorous TEMPO derivatives is reported, along with their fluorous-organic solvent partition coefficients and their ESR spectra. Applications of the fluorous-TEMPO reagents in oxidation reactions and as radical traps are discussed.

Samarium diiodide-catalyzed diastereoselective pinacol couplings

(Chemical Equation Presented) A complex of samarium diiodide (Sml 2) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me2SiCl2 and Mg. Diastereoselectivity of up to 95/5 (±/meso) has been achieved for aliphatic aldehydes and up to 19/81 (±/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the Sml 2/tetraglyme/Mg/Me2SiCl2 catalytic system.