62102-73-2

Upstream product

• 108-85-0 1-bromocyclohexane 
• 467238-80-8 cyclohexane-1,1-[2H,2H]-methanol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 80783-98-8 N-methoxy-N-methylcyclohexanecarboxamide 

Downstream Products

• 135512-98-0 naphthalen-2-ylmethyl 2-naphthoate 
• 1228389-66-9 C₂₂H₁₄⁽²⁾H₂O₂ 

Relevant academic research and scientific papers

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimenthylsily)diazomethane in a regiospecific and highly stereoselective manner

The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright

Metal-free CH bond activation of branched aldehydes with a hypervalent iodine(III) catalyst under visible-light photolysis: Successful trapping with electron-deficient olefins

Direct acyl radical formation of linear aldehydes (RCH2-CHO) and subsequent hydroacylation with electron-deficient olefins can be effected with various types of metal and nonmetal catalysts/reagents. In marked contrast however no successful reports on the use of branched aldehydes have been made thus far because of their strong tendency of generating alkyl radicals through the facile decarbonylation of acyl radicals. Here use of a hypervalent iodine(III) catalyst under visible light photolysis allows a mild way of generating acyl radicals from various branched aldehydes thereby giving the corresponding hydroacylated products almost exclusively. Another characteristic feature of this approach is the catalytic use of hypervalent iodine(III) reagent which is a rare example on the generation of radicals in hypervalent iodine chemistry.

Mild and selective hydrozirconation of amides to aldehydes using Cp 2Zr(H)Cl: Scope and mechanistic insight

An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.

One-step facile synthesis of deuterium labeled aldehydes from tertiary amides using Cp2Zr(D)Cl

The synthesis of deuterium labeled aldehydes was accomplished in an expedient and facile manner through the reduction of amides using commercially available Cp2Zr(D)Cl. The reactions proceeded rapidly (ca. 15min) and in high yields (70-99%).

A New Synthesis of Aldehydes and Aldehydes-d from Grignard Reagents

Aldehydes were prepared from Grignard reagents in high yields using pentacarbonyliron as the carbonylating agent.This reaction was also found to be applicable to the synthesis of aldehydes-d.