137407-47-7

Upstream product

• 931-88-4 cis-Cyclooctene 
• 114895-10-2 phenylazoxy phenyl sulphone 
• 16538-85-5 phenylcyclooctane 
• 7287-06-1 1-phenyl-1-cyclooctanol 
• 93-97-0 benzoic acid anhydride 
• 61815-42-7 (E)-1-Bromo-cyclooctene 
• 28075-35-6 1-cyclooctenyl triflate 
• 100-58-3 phenylmagnesium bromide 
• 502-49-8 cycloactanone 
• 931-88-4 1,2-cyclooctene 
• 29974-69-4 trans-1,2-dibromocyclooctane 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 14922-16-8 phenylazo phenyl sulfone 

Downstream Products

• 92-52-4 biphenyl 
• 16538-85-5 phenylcyclooctane 
• 29304-32-3 8-oxo-8-phenyloctanal 
• 39755-15-2 8-oxo-8-phenyloctanenitrile 
• 98-86-2 acetophenone 
• 24314-23-6 8-oxo-8-phenyloctanoic acid 
• 103187-10-6 8-hydroxy-8-phenyloctanoic acid 
• 413615-54-0 8-hydroxy-1-phenyl-1-octanone 
• 6004-52-0 cycloheptyl(phenyl)methanone 
• 14996-79-3 2-phenylcyclooctan-1-one 

Relevant academic research and scientific papers

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

Heck reactions without salt formation: Aromatic carboxylic anhydrides as arylating agents

Environmentally benign and economical production of arylated olefins can be achieved by a new variant of the Heck reaction in which no halogen salts are formed. The trick is the use of aromatic carboxylic anhydrides 1 as arylating agents. With halide-activated palladium chloride as catalyst, which requires no phosphane ligands, the olefins 2 can be prepared according to Equation (a) in good yields.

Thermochemistry of Strained Cycloalkenes: Experimental and Computational Studies

Pulsed time-resolved photoacoustic calorimetry in combination with quantum yield determinations afforded the relaxed triplet energy of 1-phenylcyclooctene and the energy of geometric isomerization of cis-1-phenylcyclooctene.These values are combined with

Selective one-pot carbon-carbon bond formation by catalytic boronation of unactivated cycloalkenes and subsequent coupling

(Chemical Equation Presented) Two channels: Cycloalkenes can be selectively functionalized by iridium-catalyzed boronation followed by Suzuki coupling with an aryl iodide or reaction with an aldehyde. The selectivity for allylic and vinylic functionalization can be controlled by a slight change of the reaction conditions. DBU = 1,8-diazabicyclo-[5.4.0]undec-7-ene, pin = pinacol.

One-pot synthesis of substituted styrenes from vicinal dibromoalkanes and arylboronic acids

Dehydrobromination of vicinal dibromoalkanes in systems comprising 1,2-dimethoxy-ethane, N-butyl-N′-methylimidazolium tetrafluoroborate (or tetrabutylammonium bromide), and a base with subsequent palladium-catalyzed cross-coupling of the thus formed bromoalkenes with arylboronic acids furnished substituted styrenes. Springer Science+Business Media, Inc. 2007.

METHOD FOR PRODUCING COMPOUND THROUGH COUPLING

Disclosed is a method for producing a compound (D) through coupling by subjecting an organic compound (A) having a leaving group and an organic metal compound or metal hydride compound (B) to a coupling reaction. This method is characterized in that the organic compound (A) having a leaving group and the organic metal compound or metal hydride compound (B) are reacted with each other in the presence of a catalyst composition (C) containing a transition metal compound (C-1) and a ligand (C-2) which has a coordinating group and a protic group in such a manner that the coordinating group and the protic group are next to each other. This method is useful for efficiently producing a compound through coupling.

Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation

Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf ? ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism. Copyright

Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes

Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.

Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system catalyses efficiently the Heck reaction of aryl halides with linear alkenes such as pent-1-ene, oct-1-ene or dec-1-ene. Selectivities up to 70% in favour of E-1-arylalk-1-ene isomers can be obtained. In the presence of cyclic alkenes the selectivities of the reactions strongly depends on the ring size. Addition to cyclohexene or cycloheptene led mainly to 1-arylcycloalk-3-ene derivatives. On the other hand, addition to cyclooctene led to 1-arylcycloalk-1-ene adducts.

Novel Diradical-Mediated Ring Opening Reactions

Thermo-isomerization of medium- and large-ring 1-phenylcycloalkanols 1e-i at around 650 deg C in a flow reactor system delivers the open-chain phenones 4e-i. A reaction mechanism via an open-chain diradical intermediate, followed by an intramolecular hydrogen transfer is proposed. Thermo-isomerization of α-substituted 1-phenylcyclododecanols 6 proceeds regioselectively under the formation of ω-substituted phenones 7. Furthermore, this novel hydrogen transfer reaction provides a new access to ω-substituted fatty acids.