335259-42-2

Upstream product

• 930-68-7 cyclohexenone 
• 63503-60-6 3-chlorophenylboronic acid 
• 7519-92-8 tris(3-chlorophenyl)boroxine 
• 56917-71-6 5-trimethylsilyl-2-cyclohexanone 
• 108-37-2 1-bromo-3-chlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 108-94-1 cyclohexanone 
• 1416277-01-4 (3-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate 

Relevant academic research and scientific papers

Chiral bidentate bis(N-heterocyclic carbene)-based palladium complexes bearing carboxylate ligands: Highly effective catalysts for the enantioselective conjugate addition of arylboronic acids to cyclic enones

Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes with two weakly coordinating carboxylate ligands are effective catalysts for the asymmetric conjugate addition of arylboronic acids to cyclic enones, producing the corresponding adducts in moderate-to-high yields and with good-to-high enantioselectivities, in most cases under mild conditions.

Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones

Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1

Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.

Asymmetric Baeyer-Villiger oxidation: Classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of: Meso -disubstituted cycloketones

Regioselectivity is a crucial issue in Baeyer-Villiger (BV) oxidation. To date, few reports have addressed asymmetric BV oxidation of 3-substituted cycloketones due to the high difficulty of controlling regio- and stereoselectivity. Herein, we report the asymmetric BV oxidation of 3-substituted and meso-disubstituted cycloketones with chiral N,N′-dioxide/Sc(iii) catalysts performed in three ways: classical kinetic resolution, parallel kinetic resolution and desymmetrization. The methodology was applied in the total and formal synthesis of bioactive compounds and natural products. Control experiments and calculations demonstrated that flexible and adjustable catalysts played a significant role in the chiral recognition of substrates.

Electronic and Steric Tuning of an Atropisomeric Disulfoxide Ligand Motif and Its Use in the Rh(I)-Catalyzed Addition Reactions of Boronic Acids to a Wide Range of Acceptors

A novel chiral disulfoxide ligand pair bearing fluorine atoms at the 6 and 6′ position of its atropisomeric backbone, (M,S,S)- and (P,S,S)-p-Tol-6F-BIPHESO, was synthesized. Complexation to a rhodium(I) precursor gave rise to μ-Cl- and μ-OH-bridged rhodiu

Palladium-catalyzed redox cascade for direct β-arylation of ketones

Herein we report a full article about the detailed design and development of two palladium-catalyzed redox cascade methods that enable direct β-arylation of ketones. Palladium-catalyzed ketone dehydrogenation, aryl-X bond activation and conjugate addition were merged into a redox-neutral catalytic cycle. Non-metal-based aryl electrophiles were used as both the oxidant and the aryl source. The β-arylation with aryl iodides was achieved site-selectively with Pd(TFA)2/P(i-Pr)3 as the precatalyst and AgTFA as the iodide scavenger. Both cyclic and linear ketones can react to give β-aryl ketones with excellent functional group tolerance. The β-arylation with diaryliodonium salts was realized without stoichiometric heavy metal additives, and proved to be redox-neutral. A wider substrate scope regarding aryl groups and ketones was obtained for the arylation with diaryliodonium salts, and the possible involvement of palladium nanoparticles as the active catalyst was examined and discussed.

A New Type of Chiral Cyclic Sulfinamide–Olefin Ligands for Rhodium-Catalyzed Asymmetric Addition

A new type of chiral cyclic sulfinamide–olefin ligands, N-allylic 2,3-dihydro-1,2-benzoisothiazole 1-oxides, with 2,3-dihydro-1,2-benzoisothiazole 1-oxide as a unique chiral skeleton, is developed for the highly enantioselective rhodium-catalyzed asymmetr

Two phenyls are better than one or three: Synthesis and application of terminal olefin-oxazoline (TOlefOx) ligands

A novel terminal olefin-oxazoline ligand was introduced into rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to enones and gave excellent enantioselectivities. The two phenyls proved better than one or three in ligand evaluations.

2-allyl-1-oxo-2, 3-dihydro-1, 2-benzisothiazole

The invention discloses chiral 2-allyl-1-oxo-2, 3-dihydro-1, 2-benzisothiazole and its preparation method and use. The chiral 2-allyl-1-oxo-2, 3-dihydro-1, 2-benzisothiazole is a racemate or an optical isomer shown in the formula I and is characterized in

DIRECT B-ARYLATION OF CARBONYL COMPOUNDS

Disclosed is a method for the β-C—H H functionalization of carbonyl compounds that is both selective and broadly applicable. The methods provide direct β-arylation of carbonyl compound with a diverse array of aryl or heteroaryl halides, aryl or heteroryl tosylate, aryl or heteroaryl triflates, or diaryliodonium salts, by palladium catalysis in the presence of a ligand and promoter.