35192-31-5

Upstream product

• 611-15-4 1-methyl-2-vinyl-benzene 
• 7287-82-3 1-O-tolyl-ethanol 
• 577-16-2 2-Methylacetophenone 
• 14994-03-7 tris(benzyl)aluminum 
• 74-86-2 acetylene 
• 55968-39-3 1-(1-chloroethyl)-2-methylbenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 946089-43-6 4,5-dimethyl-2-(o-tolyl)-1(4H)-naphthalenone 

Relevant academic research and scientific papers

Dehydrative Coupling of Benzylic Alcohols Catalyzed by Br?nsted Acid/Lewis Base

Traditional cross-coupling reactions show some disadvantages like the use of organohalides or the production of stoichiometric amounts of waste. The dehydrative homo- or heterocoupling of alcohols therefore arises as an interesting approach for a highly atom-economical formation of carbon–carbon bonds, since water is produced as the only by-product. We herein report a simple and direct, metal-free protocol for the synthesis of olefins by applying catalytic amounts of a sulfonic acid and triphenylphosphane under air. A variety of olefins could be synthesized from benzylic alcohols under relatively mild conditions. Additionally, dehydrative hydroarylation of benzylic alcohols with electron-rich arenes was possible by using only Br?nsted acid under otherwise same reaction conditions. We could show that phosphane additives are essential to overcome oligomerization as main side reaction by the occupancy of the reactive carbocation intermediate.

Highly efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes

A convenient and efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of higher olefins in good to excellent yields.

Efficient hydroarylation and hydroalkenylation of vinylarenes by Br?nsted acid catalysis

Br?nsted acid Tf2NH alone catalyzed Friedel-Crafts-type hydroarylation and head-to-tail hydroalkenylation of vinylarenes under mild reaction conditions have been realized, providing a readily scalable, metal-free, and practical access to the 1,1-diarylalkane scaffolds and trans-1,3-diaryl-1-butenes in high yields and excellent regioselectivities.

Iron-catalyzed stereospecific olefin synthesis by direct coupling of alcohols and alkenes with alcohols

Chemical equations presented. An efficient Fe(III)-catalyzed direct coupling of alkenes with alcohols and cross-coupling of alcohols with alcohols to give the corresponding substituted (E)-alkenes stereospecifically is demonstrated. Additionally, this reaction could be scaled up. The kinetic isotope effect (KIE) experiments indicated a typical secondary isotope effect in this process. Although benzylic alcohols were effective substrates, mild conditions, atom efficiency, environmental soundness, and stereospecificity are features that make this procedure very attractive.

Highly efficient Pd(acac)2/TFA catalyzed head-to-tail dimerization of vinylarenes at room temperature

Pd(acac)2 catalyzed dimerization of vinylarenes to form dimers under mild condition with excellent yields and stereoselectivities. In particular, the use of TFA highly promoted the activity and selectivity of the dimerization. The studies on mechanism for the reaction displayed clearly that the dimerization of styrenes is 100% atom economic reaction.

Iron-catalysed regio- And stereoselective head-to-tail dimerisation of styrenes

Cationic iron salts and complexes catalyse the head-to-tail dimerisation of styrene derivatives to form the corresponding dimers with good to excellent yields and stereoselectivities. In particular, the use of a phosphine-iron(III) complex allows the recovery and reuse of the catalyst. The counteranion plays an important role in both the activity and selectivity. These catalysts constitute an alternative to those based on toxic and expensive late-transition metals.

A new type of carbonylation of styrenes catalyzed by Pd(OAc)2 combined with molybdovanadophosphate

A new type of carbonylation of styrenes was achieved under a 1:1 mixture of CO (0.5 atm) and O2 (0.5 atm) in the presence of Pd(OAc)2 combined with H5PMo10V2O40 nH 2O to give 4-methyl-2-phenylnaphthalen-1(4H)-one in 78% yield. Various substituted styrenes were also carbonylated to the corresponding substituted arylnaphthalen-l(4H)-ones in moderate yields. The reaction was found to proceed in two stages involving the head-to-tail dimerization of styrenes, followed by carbonylation of the resulting dimers. Styrenes were efficiently dimerized under air (1 atm) in the absence of CO even at room temperature to produce head-to-tail dimers in good yields.