93725-77-0

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 62701-99-9 diphenyl 4-(tert-butyl)cyclohex-1-en-1-yl phosphate 
• 106-38-7 para-bromotoluene 
• 5720-05-8 4-methylphenylboronic acid 
• 77412-96-5 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 
• 611235-47-3 toluene-4-sulfonic acid 4-tert-butylcyclohex-1-en-1-yl ester 

Relevant academic research and scientific papers

N-tosylhydrazones as reagents for cross-coupling reactions: A route to polysubstituted olefins

Metal-free partner: No organometallic coupling partner is required for a Pd-catalyzed cross-coupling reaction that employs N-tosylhydrazones as the nucleophilic component (see scheme; Ts = 4-toluenesulfonyl).

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.

A ligand free and room temperature protocol for Pd-catalyzed kumada-corriu couplings of unactivated alkenyl phosphates

Kumada - Corriu cross-couplings of nonactivated cyclic and acyclic vinyl phosphates with aryl magnesium reagents afforded a series of 1,1-disubtituted alkenes in good yields for most cases when the reactions were performed at room temperature with the sim

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.

Kumada coupling of aryl and vinyl tosylates under mild conditions

Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.

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 Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates

The cross-coupling reaction of 9-alkyl-9-borabicyclononane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields.The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained.The utility of the present reaction was demonstrated by the cyclization of ω-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration intramolecular coupling sequence.