112176-17-7

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• 106-38-7 para-bromotoluene 
• 76644-52-5 rac-3-acetoxycyclohexene 
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• 5720-05-8 4-methylphenylboronic acid 
• 110-83-8 cyclohexene 
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• 1393561-44-8 3-(4-methylphenyl)thiepane 1,1-dioxide 
• 25057-68-5 thiepan-3-one 
• 19090-03-0 dihydro-2H-thiopyran-3(4H)-one 

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• 644-08-6 4-Methylbiphenyl 

Relevant academic research and scientific papers

Transition-metal-free one-pot synthesis of biaryls from grignard reagents and substituted cyclohexanones

A new strategy for the construction of biaryls by a transition-metal-free process is presented. A sequence of a Grignard reaction, dehydration, and oxidative aromatization affords the desired products in a one-pot fashion. Copyright

Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids

Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.

Iron phosphine catalyzed cross-coupling of tetraorganoborates and related group 13 nucleophiles with alkyl halides

Iron phosphine complexes prove to be good precatalysts for the cross-coupling of alkyl, benzyl, and allyl halides with not only aryl triorganoborate salts but also related aluminum-, gallium-, indium-, and thallium-based nucleophiles. Mechanistic studies revealed that while Fe(I) can be accessed on catalytically relevant time scales, lower average oxidation states are not formed fast enough to be relevant to catalysis. EPR spectroscopic studies reveal the presence of bis(diphosphine)iron(I) complexes in representative catalytic reactions and related processes with a range of group 13 nucleophiles. Isolated examples were studied by M?ssbauer spectroscopy and single-crystal X-ray structural analysis, while the electronic structure was probed by dispersion-corrected B3LYP DFT calculations. An EPR study on an iron system with a bulky diphosphine ligand revealed the presence of an S = 1/2 species consistent with the formation of a mono(diphosphine)iron(I) species with inequivalent phosphine donor environments. DFT analysis of model complexes allowed us to rule out a T-shaped Fe(I) structure, as this is predicted to be high spin.

Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

Enantioselective synthesis of chiral sulfones by ir-catalyzed asymmetric hydrogenation: A facile approach to the preparation of chiral allylic and homoallylic compounds

A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Baecklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).

Ion-tagged π-acidic alkene ligands promote Pd-catalysed allyl-aryl couplings in an ionic liquid

Ionic π-acidic alkene ligands based on chalcone and benzylidene acetone frameworks have been ?doped? into ionic liquids to provide functional reaction media for Pd-catalysed cross-couplings of a cyclohexenyl carbonate with aryl siloxanes that allow simple product isolation, free from Pd (50 ppm) and ligand contamination.

Efficient palladium-catalyzed nucleophilic addition of triorganoindium reagents to carbocyclic derivatives

Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd2(dba)3 to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.

Palladium-catalyzed arylation of allylic benzoates using hypervalent siloxane derivatives

Palladium-catalyzed cross-coupling of hypervalent arylsiloxane derivatives proceeded in good to excellent yields with allylic benzoates. Arylation occurred with complete inversion of configuration. The scope and limitations of this reaction, an alternative to the Stille coupling, is summarized.

Tailoring aqueous solvents for organic reactions: Heck coupling reactions in high temperature water

High temperature water is demonstrated to be an effective solvent for Heck coupling reactions of aromatic halides with cyclic alkenes without the addition of co-solvents or specialized ligands. Reactions in the presence of LiCl and quaternary ammonium salts indicate that the reaction takes place in the aqueous phase.

Reactions of Azo and Azoxy Sulphones with Transition Metal Complexes. Part 7. Arylation of Olefins with Arylazoxy Aryl Sulphones Catalysed by a Palladium(0) Phosphine Complex

The arylation of acyclic and cyclic olefins by arylazoxy aryl sulphones has been investigated in the presence of a palladium(0) catalyst in benzene.Both of the aryl groups of the arylazoxy aryl sulphones are found to participate in the arylation.Two equivalents of aryl-substituted olefins were obtained when the reactions were carried out at 80 deg C, whereas one equivalent of olefin was arylated at 120 deg C.A plausible catalytic cycle involving a diarylpalladium(II) species is proposed.