22875-84-9

Upstream product

• 100-42-5 styrene 
• 56800-08-9 1,3-dichloro-1-butene 
• 2909-32-2 pyridine-2-carboxylic acid (1-phenyl-ethyl)amide 
• 2909-34-4 N-(1-phenylethyl)isonicotinamide 
• 501-65-5 diphenyl acetylene 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 100-46-9 benzylamine 
• 29817-09-2 1-methylene-2-phenylcyclopropane 
• 100-58-3 phenylmagnesium bromide 
• 98-81-7 1-bromovinylbenzene 
• 1524-12-5 1-phenylethyl 2,2,2-trifluoroacetate 
• 34804-73-4 4,5-diphenyl-3,6-dihydro-1,2-dithiin 

Downstream Products

• 1857-74-5 2,3-diphenylbutane 
• 782-05-8 (Z)-2,3-diphenyl-2-butene 
• 782-06-9 (E)-2,3-diphenylbutene 

Relevant academic research and scientific papers

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Scope and mechanism of homogeneous tantalum/iridium tandem catalytic alkane/alkene upgrading using sacrificial hydrogen acceptors

An in-depth investigation of a dual homogeneous catalyst system for the coupling of alkanes and alkenes based on an early-/late-transition-metal pairing is reported. The system is composed of Cp*TaCl2(alkene) for alkene dimerization and pincer-iridium hydrides for alkane/alkene transfer hydrogenation. Because there is no kinetically relevant interaction between the two catalysts, the tandem mechanism can be entirely described using the two independent catalytic cycles. The alkene dimerization mechanism is characterized by an entropically disfavored pre-equilibrium between Cp*TaCl 2(1-hexene) + 1-hexene and Cp*TaCl 2(metallacyclopentane) (ΔH° = -22(2) kcal/mol; ΔS° = -16(2) eu); thus, the overall rate of alkene dimerization is positive order in 1-hexene (exhibiting saturation kinetics), and increases only modestly with temperature. In contrast, the rate of 1-hexene/n-heptane transfer hydrogenation catalyzed by t-Bu[PCP]IrH4 is inverse order in 1-hexene and increases substantially with temperature. Styrene has been investigated as an alternate sacrificial hydrogen acceptor. Styrene dimerization catalyzed by Cp*TaCl2(alkene) is considerably slower than 1-hexene dimerization. The conversion of styrene/heptane mixtures by the Ta/Ir tandem system leads to three product types: styrene dimers, coupling of styrene and heptane, and heptene dimers (from heptane). Through careful control of reaction conditions, the production of heptene dimers can be favored, with up to 58% overall yield of heptane-derived products and cooperative TONs of up to 12 and 10 for Ta and Ir catalysts, respectively. There is only slight inhibition of Ir-catalyzed styrene/n-heptane transfer hydrogenation under the tandem catalysis conditions.

TANDEM TRANSFER HYDROGENATION AND OLIGOMERIZATION FOR HYDROCARBON PRODUCTION

The disclosure provides for hydrocarbon production by hydrogenation and oligomerizaton and, more particularly, to catalysis of alkanes and alkenes by a tandem transfer hydrogenation and oligomerization.

TERMINAL 1,1-DISUBSTITUTED ALKENES, METHOD OF MAKING AND USING THEREOF

Disclosed is a process for preparing terminal 1,1-disubstituted alkenes and is to compounds prepared therewith.

"On water" sp3-sp2 cross-couplings between benzylic and alkenyl halides

Organic-solvent-free cross-couplings between benzylic and alkenyl halides have been developed. Various alkenyl halides can be efficiently benzylated by combining the precursor halides in the presence of Zn dust and a Pd catalyst at room temperature, in water as the only medium.

Silica-supported KHSO4: An efficient system for activation of aromatic terminal olefins

Potassium hydrogen sulfate adsorbed on chromatography-grade silica gel activates electron-rich aromatic terminal olefins towards nucleophilic attack at the benzylic position by alcohols. Temperature plays a crucial role and facilitates suppressing nucleophilic reaction in favor of dimerization of the terminal olefin. Georg Thieme Verlag Stuttgart - New York.

Catalytic intermolecular tail-to-tail hydroalkenylation of styrenes with α olefins: Regioselective migratory insertion controlled by a nickel/n-heterocyclic carbene

Making head or tail of it: The first single-operation, highly selective intermolecular tail-to-tail hetero-hydroalkenylation from two readily available monosubstituted alkenes is described (see scheme; IPr=1,3-Bis(2,6-di- isopropylphenyl)imidazol-2-ylidene). The reaction is catalyzed by the proposed [(IPr)NiH]OTf species. The method allows the use of more common and structurally diverse α olefins as substrates, which were previously not compatible with known methods. Copyright

Zinc chloride enhanced arylations of secondary benzyl trifluoroacetates in the presence of b-hydrogen atoms

Zinc or swim: Arylation of benzyl trifluoroacetates with arylzinc reagents in the presence of β- hydrogen atoms were realized under mild conditions. Both electron-rich and electron-deficient arene substrates were successfully arylated. This arylation method could offer a very versatile synthetic route to access a series of diversity-oriented diarylalkane motifs. TFA = trifluoroacetyl. Copyright

Nickel-catalyzed regioselective carbomagnesation of methylenecyclopropanes through a site-selective carbon-carbon bond cleavage

chemical equation presented Unwringing the ring: Methylenecyclopropanes reacted with vinyl and aryl Grignard reagents in the presence of a nickel catalyst to afford vinyl- and arylmagnesation products, respectively, through a selective C - C bond cleavage (see scheme). The reaction provides a new method for the preparation of substituted homoallyl and allyl Grignard reagents.

Quest for diatomic selenium

Metallocene pentaselenides and elemental selenium were employed in an effort to generate diatomic selenium (Se2) under thermal conditions. Trapping experiments were carried out with six dienes. A successful formation of a diselenium adduct was observed in the case of 5,6-dimethylene-cyclohexa-1,3- diene (1a). The other dienes produced the corresponding dihydroselenophenes. The in-depth study of the limitations of our method to generate Se2 is described; a plausible mechanism rationalizing the observed results is proposed.