33061-20-0

Upstream product

• 960-16-7 tributylphenylstannane 
• 77412-96-5 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 96133-27-6 4-tert-butyl-1-iodo-1-cyclohexene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 611235-47-3 toluene-4-sulfonic acid 4-tert-butylcyclohex-1-en-1-yl ester 

Downstream Products

• 87830-07-7 r-1-(4-methoxyphenyl)-1,t-2-difluoro-t-4-tert-butylcyclohexane 
• 87830-01-1 r-1-(4-methoxyphenyl)-1,c-2-difluoro-t-4-tert-butylcyclohexane 

Relevant academic research and scientific papers

Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis

A direct (3+2) cycloaddition between alkenes and vinyl diazo reagents using either Cr or Ru photocatalysis is described. The intermediacy of a radical cation species enables a nucleophilic interception by vinyl diazo compounds, a departure from their trad

Well-defined air-stable palladium HASPO complexes for efficient Kumada-Corriu cross-couplings of (Hetero)aryl or alkenyl tosylates

Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.

Atom-efficient vinylic arylations with triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis

The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times.

Pd-catalyzed cross-coupling reactions with carbonyls: Application in a very efficient synthesis of 4-aryltetrahydropyridines

A method is proposed to prepare 4-aryltetrahydropyridines by a Pd-catalyzed cross-coupling reaction by using tosylhydrazone as the nucleophilic coupling agent without stoichiometric organometallic reagent. Palladium-catalyzed couplings can be used for the formation of C-C linkages. It was observed during study that tosylhydrazone can be generated by employing 4-piperidones directly in the cross-coupling reaction with tetrahydropyridines in very high yields. It was also found during study that the ketones and aldehydes can be employed as nucleophilic coupling partners in a reaction without using stoichiometric organometallic reagent. The study concluded that the method can be used to prepare different types of di- and trisubstituted olefins at large scale.

Chemoselective elimination of iodine azide - Directivity effect of the t-butyl group

Iodine azide adducts of 1-aryl-4-t-butylcyclohexenes on treatment with ethanolic potassium hydroxide undergo the chemoselective elimination of iodine azide and not the expected hydrogen iodine elimination.

Palladium-Catalyzed Coupling of Arylstannanes with Organic Sulfonates: A Comprehensive Study

The effect of ligands and lithium chloride on the rates of the palladium catalyzed coupling between organic triflates and arylstannanes was studied.The dependence of the rate on the ligand is similar to the one previously reported for the coupling of vinylstannanes, but in the present case triphenylarsine is shown to be superior to both triphenylphosphine and tri(2-furyl)phosphine.The effect of added chloride is complex and varies depending on solvent and ligand used.Ortho-substituted arylstannanes tend to transfer alkyl moieties to a substantial extent, andtherefore rates and efficiencies of aryl vs alkyl transfer were quantitated.When ortho substituents that are potentially coordinating to tin are used, no rate acceleration in the alkyl transfer process was observed, which is in contrast with two recently reported studies that suggest nucleophilic assistance at tin to be important in the transmetalation step.An important side reaction in the coupling of poorly reactive vinyltriflates and most aryltriflates is the Pd-induced homocoupling of the stannane to form biaryls.The experimental factors that control this process were evaluated.

Catalyst tailoring for palladium-mediated cross coupling of arylstannanes with vinyl triflates

Vinyl triflates couple smoothly with a variety of arylstannanes provided a polar, aprotic solvent is used in conjunction with a "ligandless" palladium catalyst, or catalytic system involving weak ligands such as triphenylarsine. Commonly employed ligands, for example, triphenylphosphine, were found to strongly inhibit the coupling.