137058-15-2

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 108-94-1 cyclohexanone 

Downstream Products

• 197293-01-9 6-iodo-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 932393-75-4 5-(tert-butyl-dimethyl-silanyloxy)-1-(2-phenyl-cyclohex-1-enyl)-pent-1-yn-3-ol 
• 932393-59-4 5-(2-phenylcyclohex-1-enyl)penta-3,4-dien-1-ol 
• 932393-60-7 3-methyl-5-(2-phenylcyclohex-1-enyl)hexa-3,4-dien-1-ol 
• 932393-57-2 [2-(2-cyclopentylidene-1-methylvinyl)cyclohex-1-enyl]benzene 
• 932393-74-3 acetic acid 1-(2-phenyl-cyclohex-1-enylethynyl)-cyclopentyl ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Annulation of Internal Alkynes by Arene-Containing Vinylic Iodides and Triflates

In the presence of a palladium catalyst, internal alkynes undergo carboannulation by cyclic and acyclic vinylic iodides and triflates bearing a neighboring aromatic ring to produce a variety of carbocycles. For example, a number of 9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have been prepared in good yields through the palladium-catalyzed annulation of internal alkynes by 2-phenyl-1-cyclohexenyl triflate (1) or l-iodo-2-phenylcyclohexene (2). This annulation process is fairly general and highly regioselective. The process appears to involve oxidative addition of the vinylic substrate to Pd(0) to produce a vinylic palladium intermediate, which adds the carbon moiety to the less hindered end and the palladium to the more hindered end of the alkyne, followed by intramolecular ring closure onto the neighboring aryl group. The scope and limitations of this methodology are discussed.

Steric effects on deprotonative generation of cyclohexynes and 1,2-cyclohexadienes from cyclohexenyl triflates by magnesium amides

Steric effects on the deprotonative generation of cyclohexynes and 1,2-cyclohexadienes from cyclohexenyl triflates are described. A cyclohexenyl triflate, which is readily available from nonsubstituted cyclohexanone, was selectively converted to cyclohexy

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines

An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.

Achieving Site Selectivity in Metal-Catalyzed Electron-Rich Carbene Transfer Reactions from N-Tosylhydrazones

Catalyst control of the site-selectivity of electron-rich alkyl, aryl disubstituted carbenes generated in situ from o-alkenyl-substituted N-tosylhydrazones was achieved in this study. Exposure of these substrates to copper iodide triggered the formation of α-alkoxy 2H-naphthalenones. This investigation established that changing the catalyst to a rhodium(II) carboxylate turned off cyclization and migration of the electron-rich metal carbene with the β-carboxylate and turned on allylic C-H bond functionalization to diastereoselectively afford 1H-indenes. Examination of the scope of this reaction revealed that ethereal, aminomethylene, and unactivated 2° C-H bonds could be functionalized.

Synthetic and Computational Studies on the Rhodium-Catalyzed Hydroamination of Aminoalkenes

The influence of ligand structure on rhodium-catalyzed hydroamination has been evaluated for a series of phosphinoarene ligands. These catalysts have been evaluated in a set of catalytic intramolecular Markovnikov hydroamination reactions. The mechanism o

Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles

The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.

Preparation of alkylmagnesium reagents from alkenes through hydroboration and boron-magnesium exchange

Tolerant: Alkylmagnesium reagents can be synthesized from alkenes through a sequence of hydroboration and subsequent boron-magnesium exchange using a method that tolerates different functional groups (see scheme). The resulting alkylmagnesium reagents can be used in carbon-carbon bond forming reactions, such as alkylation reactions or transition-metal-catalyzed cross-coupling reactions. Copyright

Palladium-catalyzed cyclocoupling of 2-halobiaryls with isocyanides via the cleavage of carbon-hydrogen bonds

(Figure Presented) To demonstrate the utility of isocyanides in catalytic C-H bond functionalization reactions, a palladium-catalyzed cyclocoupling reaction of 2-halobiaryls with isocyanides was developed. The reaction afforded an array of fluorenone imine derivatives via the cleavage of a C-H bond at the 2′-position of 2-halobiaryls. The use of 2,6-disubstituted phenyl isocyanide was crucial for this catalytic cyclocoupling reaction to proceed. The reaction was applicable to heterocyclic and vinylic substrates, allowing the construction of a wide range of ring system. The large kinetic isotope effect observed (kH/kD = 5.3) indicates that C-H bond activation was the turnover-limiting step in this catalysis.

7-SUBSTITUTED INDOLE MCL-1 INHIBITORS

Compounds which inhibit the activity of anti-apoptotic Mcl-1 protein, compositions containing the compounds, and methods of treating diseases involving overexpressed or unregulated Mcl-1 protein are disclosed