66262-12-2

Upstream product

• 3761-92-0 n-hexylmagnesium bromide 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 61476-98-0 7-tosyl-1,4-dioxaspiro[4.5]decane 
• 44767-62-6 n-hexylmagnesium chloride 
• 111-25-1 1-bromo-hexane 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 504-02-9 1,3-cylohexanedione 
• 57918-73-7 3-acetoxy-cyclohex-2-enone 
• 130654-97-6 1-hexylcyclohex-2-enol 
• 638-45-9 1-Iodohexane 
• 82235-19-6 7-Hexyl-7-(toluene-4-sulfonyl)-1,4-dioxa-spiro[4.5]decane 
• 930-68-7 cyclohexenone 
• 66-25-1 hexanal 
• 81925-48-6 6-Hexyl-2-methoxy-2-methyl-3,4-dihydro-2H-pyran 

Downstream Products

• 1199807-41-4 (+)-(S)-3-hexyl-3-methylcyclohexanone 

Relevant academic research and scientific papers

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

IBS-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxone

A 2-iodoxybenzenesulfonic acid (IBS)-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with powdered Oxone in the presence of potassium carbonate and tetrabutylammonium hydrogen sulfate has been developed.

Copper-catalyzed asymmetric conjugate addition with chiral SimplePhos ligands

SimplePhos ligands represent a novel class of monodentate chiral ligands based on a chiral amine moiety and flexible diaryl groups on the phosphorous atom. They can be easily prepared by two different pathways and they can be highly functionalised. Herein we report the copper-catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro-olefins, with up to 98.6 % ee. Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3substituted enones, thus allowing the formation of stereogenic quaternary carbon centres.

Cross-coupling of alkenyl/aryl carboxylates with grignard reagent via Fe-catalyzed C-O bond activation

(Chemical Equation Presented) Iron-catalyzed cross-coupling of alkenyl/aryl carboxylates with primary alkyl Grignard reagent was described. This reaction brought a new family of electrophiles to iron catalysis. The combination of an inexpensive carboxylat

Carbonyl transposition on organoselenium compounds

Carbonyl conjugated vinylic selenides undergo 1,3 and 1,5-carbonyl transposition sequences through organometallic reagents addition reactions followed by acid hydrolysis.

Phosphoniosilylation: An Efficient and Practical Method for the β-Functionalization of Enones

A useful procedure for the β-functionalization of enones is described in which the Wittig reaction is combined with an initial phosphoniosilylation process.

A NEW PROCEDURE FOR DESULFONYLATION: PREPARATION OF β-SUBSTITUTED α,β-UNSATURATED KETONES AND ALDEHYDES

The treatment of the tert-alkyl sulfones bearing carbonyl group at the β-position with 5 percent hydrochloric acid in THF at 30 - 65 deg C afforded β-substituted α,β-unsaturated ketones and aldehydes in excellent yields.

CYCLIC VINYL ETHER CARBANIONS-II PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL COMPOUNDS

Conditions for metalation of a variety of cyclic vinyl ethers and reaction of the resulting carbanions with electrophiles are described.Effects of the vinyl ether structure on the relative rates of metalation are discussed.Applications of this methodology