75416-78-3

Upstream product

• 39167-47-0 1,1'-bis-(4-chloro-phenyl)-2,2'-selanediyl-bis-ethanone 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 16356-02-8 1,4-dimethoxy-2-butyne 
• 99-91-2 para-chloroacetophenone 
• 21985-98-8 2,3-bis-(4-chloro-phenyl)-butane-2,3-diol 
• 1679-18-1 4-Chlorophenylboronic acid 
• 197244-15-8 but-2-yne-1,4-diyl dimethyl bis(carbonate) 
• 75230-50-1 p-chloroacetophenone tosylhydrazone 
• 89619-10-3 1-(1-bromovinyl)-4-chlorobenzene 
• 40338-30-5 dichloro-bis-(4-chloro-phenacyl)-λ⁴-selane 

Downstream Products

• 157030-87-0 4,5-di(p-chlorophenyl)-2-cyano-3,6-dihydro-2H-selenopyran 
• 10425-97-5 6-chloro-2-(4-chlorophenyl)-3-methyl-1H-indene 
• 1456822-39-1 5,6-bis(4-chlorophenyl)-2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione 
• 157031-00-0 4,5-di(p-chlorophenyl)-2-cyano-3,6-dihydro-2H-selenopyran-2-yl m-chlorobenzoate 
• 157030-99-4 3,4-di(p-chlorophenyl)-6-cyano-2H-selenopyran 

Relevant academic research and scientific papers

Copper-Catalyzed Dehydrogenative Diels-Alder Reaction

A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.

Solid Acid-Catalyzed Dehydration of Pinacol Derivatives in Ionic Liquid: Simple and Efficient Access to Branched 1,3-Dienes

The selective dehydration of pinacol derivatives to branched 1,3-dienes is extremely challenging because of the predominance of pinacol rearrangement. Herein, we successfully achieve this goal by employing a recyclable solid acid/ionic liquid catalyst system. The dehydration of alkyl- and cycloalkyl-derived diols in an Amberlyst-15/[Emim]Cl system afforded the corresponding 1,3-dienes in good yields, while a Nafion/[Emim]Cl system was demonstrated to be a better catalyst system for the dehydration of aryl-substituted substrates. Our protocol features straightforward and simple access to branched 1,3-dienes, high chemoselectivity, a recyclable catalyst system, a facile separation of dienes just by decantation, and a broad substrate scope.

From propargylic biscarbonate to diaryl[n]dendralenes

An efficient cross-coupling reaction using a low cost carbon-supported palladium (Pd/C) catalyst for the synthesis of cross-conjugated compounds, diaryl[n]dendralenes, has been developed. The reaction of a propargylic biscarbonate with phenylboronic acid using Pd/C and phosphine ligand (S-Phos) gave 2,3-diphenyl[2]dendralene in high yield. We found that Pd/C was an effective catalyst for the synthesis of dialyl[n]dendralenes. The synthesis of various dendralenes was successfully achieved under the optimized conditions, giving dialyl [2] and [4] dendralenes in good yields.

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.

Direct one-pot synthesis of 2,3-diarylbuta-1,3-diene via self-coupling of acetophenones

A mild and straightforward route to 2,3-diarylbuta-1,3-diene is described here. By treatment with SmI2-Ac20, acetophe-none and its analogues underwent self-coupling reactions and subsequent elimination to give a series of 2,3-diarylbuta-1,3-dienes in moderate to good yields.

SYNTHESES WITH DIKETO SELENIDES

We report a) a modified synthesis of diketo selenides, b) preparation of 2,5-diacylselenophenes by condensation of diketoselenides with glyoxal, c) preparation of poly-substituted selenophenes by intramolecular reductive coupling reaction of diketo selenides with low-valent titanium reagent under controlled conditions (0 degC) followed by dehydratation of the resulting 3,4-dihydroxyselenolanes, and d) formation of 2,5-dihydroselenophenes and 1,3-dienes by treatment of diketo selenides with the low-valent titanium reagent in refluxing tetrahydrofuran.

Formation of 2,5-Dihydroselenophenes and 1,3-Dienes from Diketo Selenides by Reduction with Low-valent Titanium Reagents

Reduction of a series of diketo selenides with a low-valent titanium reagent affords 2,5-dihydroselenophenes and 1,3-dienes in comparable yields.

NOVEL SYNTHESIS OF 2,3-DIARYLBUTA-1,3-DIENES FROM 1,4-DIMETHOXYBUTYNE-2

It was found that 2,3-diarylbuta-1,3-dienes were readily obtained in good to excellent yields through the SN-2' type substitution of 1,4-dimethoxybutyne-2 with aryl Grignard reagents in the presence of a copper(I) salt.