17773-62-5

Upstream product

• 2719-27-9 cyclohexanylcarbonyl chloride 
• 22966-45-6 Methyl(1-cyclohexyliden)nonyl-sulfid 
• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 626-62-0 Cyclohexyl iodide 
• 1024708-70-0 n-octyl-cyclohexyl-methanol 
• 143-33-9 sodium cyanide 
• 18394-00-8 9-octadecanone 
• 108-94-1 cyclohexanone 
• 103687-22-5 ((CH₃)3C₆H₂)2BCHLiC₇H₁₅ 
• 2043-61-0 cyclohexanecarbaldehyde 
• 629-27-6 1-Iodooctane 
• 541-41-3 chloroformic acid ethyl ester 
• 111-83-1 1-bromo-octane 

Relevant academic research and scientific papers

Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.

From Alkyl Halides to Ketones: Nickel-Catalyzed Reductive Carbonylation Utilizing Ethyl Chloroformate as the Carbonyl Source

Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid and modular synthesis of ketones remains in high demand. Described here is a nickel-catalyzed three-component reductive carbonylation method for the synthesis of dialkyl ketones. A wide range of both symmetric and asymmetric dialkyl ketones can be accessed from alkyl halides and a safe CO source, ethyl chloroformate. The approach offers complementary substrate scope to existing carbonylation methods while avoiding the use of either toxic CO or metal carbonyl reagents.

Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents

Various diaryl ketones, alkyl aryl ketones, and dialkyl ketones were efficiently prepared in good yields by the reactions of the Grignard reagents derived from aryl or alkyl bromides, followed by the reactions with aromatic or aliphatic aldehydes and the subsequent treatment with 1,3-diiodo-5,5- dimethylhydantoin and K2CO3, in a one-pot method. The same treatment of aromatic bromides bearing electron-withdrawing groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well as dialkyl ketones.

Synthesis of aliphatic ketones from allylic alcohols through consecutive isomerization and chelation-assisted hydroacylation by a rhodium catalyst

Abstract: An allylic alcohol, utilized as a precursor for an aliphatic aldehyde, reacted with olefins to afford aliphatic ketones in the presence of RhCl(PPh3)3, 2-amino-4-picoline, aniline, and benzoic acid through a tandem reaction of an isomerization and a chelation-assisted hydroacylation.

Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones

The condensation of boron stabilised carbanions, MeS2BCHLiR1, (R1≠H) with aliphatic aldehydes, R2CHO, followed by treatment with trifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an unique, broadly applicable redox process that yields ketones, R1CH2COR2, directly and in high yields. The anion MeS2BCH2Li (MeS2BCHLiR1, R1=H) gives high yields of alkenes, R2CH=CH2 in the same conditions.

Hindered Organoboron Groups in Organic Chemistry. Part 22. Some Interesting Properties of 2,4,6-Triisopropylphenylborane (Tripylborane, TripBH2, A New Useful Monoarylborane

2,4,6-Triisopropylphenylborane (tripylborane, TripBH2) is a solid, stable, hydroborating agent that hydroborates monosubstituted alkenes to give either TripBHR1 or TripBR12.TripBHR1 can be converted into mixed boranes TripBR1R2 (R1,R2 = primary alkyl, Rp) and TripBRpRs and TripBRs2 are also readily available.Oxidation of these products gives the corresponding alcohols in excellent yields, with a high selectivity for alkan-1-ols in the cases of groups derived from alk-1-enes.Cyanidation of TripBR2 proceeds to give ketones without migration of the aryl group.This establishes the low migratory aptitude of the aryl group and also that no scrambling of alkyl groups occurs.The tripyl group of TripBRp2 can be selectively removed.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Iodoalkaneswith 9-Alkyl-9-BBN Derivatives. A Direct and Selective Synthesis of Ketones

The synthesis of unsymmetrical ketones by means of the palladium-catalyzed carbonylative cross-coupling reaction of 9-alkyl-9-BBN derivatives with iodoalkanes under a carbon monoxide atmosphere is described.

HINDERED ORGANOBORON GROUPS IN ORGANIC SYNTHESIS. 13. THE DIRECT PRODUCTION OF KETONES FROM ALIPHATIC ALDEHYDES BY A UNIQUE VARIANT OF THE BORON-WITTIG REACTION

In the presence of trifluoroacetic anhydride or N-chlorosuccinimide, aliphatic aldehydes react with dimesitylboron stabilised carbanions to give after work up, the corresponding ketones, a process wich is unique among Wittig type reactions.Yields of ketones are satisfactory in all cases except those involving the anion derived from the parent compound dimesitylmethylborane, wich give the corresponding alkenes.

Reductive couplings of acid chlorides mediated by SmI2

Reductive couplings of acid chlorides and of acid chlorides with aldehydes or ketones in presence of an excess of SmI2 produce ketones in moderate to good yields.

Alkylborane complexes

The invention relates to alkylborane complexes with aromatic amines of the formula: STR1 in which R1 and R2 are the same or different (1-4C)-alkyl radicals, or together with the adjacent nitrogen atom are morpholino, piperidino or pyrrolidino radicals; R3 and R4 are independently selected from hydrogen, (1-4C)-alkyl, (1-4C)-alkoxy, di-(1-4C)-alkylamino, morpholino, piperidino and pyrrolidino; thexyl stands for 1,1,2-trimethylpropyl; and n is the integer 1 when R3 and R4 are other than nitrogen containing radicals, or the integer 1 or 2 when one of R3 and R4 is a nitrogen containing radical, or the integer 1, 2 or 3 when both R3 and R4 are nitrogen containing radicals. The complexes are more stable than thexylborane tetrahydrofuran complex, but are sufficiently reactive to be valuable as hydroborating and reducing agents. The invention also provides solutions of the complexes of formula I in organic solvents for convenient storage or subsequent synthetic use, and a process for manufacturing said complexes. A particularly convenient complex of the invention is thexylborane N,N-diethylaniline complex.