10425-96-4

Upstream product

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 19727-23-2 1,1'-dichloro-1,1'-diphenyl-1,1'-azoethane 
• 917-64-6 methyl magnesium iodide 
• 16619-12-8 2-phenyl-indan-1-one 
• 3591-42-2 1,1-dichloro-2-methyl-2-phenylcyclopropane 
• 71-43-2 benzene 
• 75-16-1 methylmagnesium bromide 
• 35099-60-6 2-methyl-3-phenylindene 
• 100-42-5 styrene 
• 2039-88-5 2-bromostyrene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 53067-92-8 2-(2-acetylphenyl)-1-phenylethan-1-one 
• 1721-96-6 1-methyl-3-phenylisoquinoline 
• 193765-94-5 Zr(Cl)2(C₉H₅(CH₃)C₆H₅)2 
• 24737-26-6 2-Fluor-1-methyl-3-phenyl-naphthalin 

Relevant academic research and scientific papers

A novel and facile synthesis of 2,3-diphenylbuta-1,3-diene

An inexpensive, simple, and high yield synthesis of the title compound is reported. In addition, some mechanistic insights into the dehydration and accompanying reactions of 2,3-diphenylbutane-2,3-diol are presented.

Hydrogen Bonding Networks Enable Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis**

Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen-bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen-bonding-assisted Br?nsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para-toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Br?nsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.

Palladium-Catalyzed Tail-to-Tail Reductive Dimerization of Terminal Alkynes to 2,3-Dibranched Butadienes

The palladium-catalyzed tail-to-tail reductive dimerization of terminal alkynes is described for the first time. Aromatic terminal alkynes bearing diverse and sensitive functional groups as well as aliphatic terminal alkynes are efficiently transformed to 2,3-dibranched butadienes. The key to achieve a selective tail-to-tail reductive dimerization reaction is to control appropriately the acidity of the reaction solution, which is accomplished by a combined use of pivalic acid and para-toluenesulfonic acid. The tail-to-tail reductive dimerization reaction is proposed to proceed via a cationic alkenyl palladium intermediate under acidic conditions.

B(C6F5)3-Catalyzed Highly Stereoselective Hydrogenation of Unfunctionalized Tetrasubstituted Olefins

A metal-free hydrogenation of unfunctionalized tetrasubstituted olefins were successfully realized using a combination of B(C6F5)3 and Ph2NMe catalyst. The corresponding products were afforded in 58-98% yields with up to >99:1 cis/trans selectivity.

Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones

A facile and highly regioselective Pd-catalyzed oxidative coupling of N-tosylhydrazones providing efficient access to 2,3-disubstituted-1,3-butadienes has been developed. This process features readily available starting materials and mild reaction conditions. Further transformations of the obtained dibranched 1,3-dienes, through Diels-Alder reactions and indene synthesis, are also demonstrated, which reveal their great potential for synthetic utility.

Synthesis of indenes via Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes

Substituted indenes can be synthesized via the Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.

Synthesis of indenes via Br?nsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes

Substituted indenes can be synthesized via the Br?nsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.

Gold(I)-catalyzed cyclodehydration enabled by the triisopropylsilyl group: A synthetically versatile methodology

Introduction of a triisopropylsilyl group into allyl and allenyl carbinols greatly enhances the efficiency of gold(I)-catalyzed cyclodehydration, which can provide rapid access to a library of various compounds including 1H-indenes (Table 2 and Scheme 5), benzofulvenes (Table 3), indan-2-ones (Scheme 2), fulvenes (Table 4), cyclopentadienes (Table 4), 5H-dibenzo[a,c][7]annulenes (Scheme 6) and dibenzosuberones (Scheme 6). The developed method enables unprecedented product generality for several classes of cyclodehydration reactions, which is particularly notable for the preparation of 1H-indenes. The first synthesis of non-benzo-fused fulvenes via cyclodehydration of allenyl vinyl carbinols could be accomplished. The protocol is remarkable for mild conditions, operational convenience, and easy access to starting materials. Copyright

Formation of five- and seven-membered rings enabled by the triisopropylsilyl auxiliary group

A highly convenient synthetic pathway to 2-indanones from aldehydes was established. The introduction of a triisopropylsilyl group greatly facilitated Meinwald rearrangement of the intermediate epoxides and alleviated the necessity of polysubstitution for the clean formation of indenes and cyclopentadienes via cyclodehydration of allylic alcohols; unprecedented freedom with respect to the product structure was thus achieved. The developed methodology could also be applicable to the formation of seven-membered rings leading to dibenzo[7]annulenes and dibenzosuberones.

Rh(I)-catalyzed reaction of 2-(chloromethyl)phenylboronic acids and alkynes leading to indenes

(Chemical Equation Presented) The reaction of 2-(chloromethyl)phenylboronic acid (1) with alkynes in the presence of a Rh(I) complex gave indene derivatives in high yields. The regioselectivity depends on the steric nature of the substituent on the alkynes. A bulky group favors the α-position of indenes.