99643-62-6

Upstream product

• 1218-89-9 4,4'-dimethylbenzoin 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 80221-11-0 1,2-bis(4-butylphenyl)ethyne 
• 32460-09-6 2,3,4,5-tetrabromofuran 
• 5720-05-8 4-methylphenylboronic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 99643-61-5 1-phenyl-2,3,4,5-tetra-p-tolylborole 

Relevant academic research and scientific papers

Reaction control in heterogeneous catalysis using montmorillonite: Switching between acid-catalysed and red-ox processes

The use of montmorillonite, modified with a super-acid (CF3SO3H), in the presence of hydroquinone as a radical scavenger and under a nitrogen atmosphere, induced the formation of tetrasubstituted furans as the major product from benzoins. In the absence of a radical scavenger, the only products obtained were 1,2-diketones.

Unexpected base-promoted synthesis of tetrasubstituted furans via palladium-catalyzed oxidation and cyclization of carbon-carbon triple bond with molecular oxygen

A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdClin DMA (N,N-dimethylacetamide)-H with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformation was investigated. Georg Thieme Verlag Stuttgart · New York.

Site-selective Suzuki-Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran

Suzuki-Miyaura reactions of 2,3,4,5-tetrabromofuran allow a convenient and site-selective synthesis of mono-, di- and tetraarylfurans which are not readily available by other methods.

Palladium-catalyzed oxidation and cyclization of carbon-carbon triple bonds in fluorous media using molecular oxygen

An intriguing, facile, and efficient oxidation and cyclization of alkynes catalyzed by Pd(OAc)2 in a fluorous biphasic system of N,N-dimethylacetamide (DMA) and perfluorodecalin directly with molecular oxygen is described, which opens an efficient access to tetrasubstituted furans. Under the optimized conditions, intermolecular reaction between diverse alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Intramolecular oxidation and cyclization of alkynes are also successfully demonstrated. The reaction proceeds efficiently under mild conditions with atmospheric oxygen as the sole oxidant. Georg Thieme Verlag Stuttgart · New York.

Synthesis of tetrasubstituted furans via sequential Pd(OAc) 2/Zn(OTf)2-catalyzed oxidation and cydization of aromatic alkynes with molecular oxygen

The development of a new method for the synthesis of tetrasubstituted furans using aromatic alkynes is reported. The strategy involves a tandem process of palladium-catalyzed oxidation and Zn(OTf)2-catalyzed cyclization in the presence of molecular oxygen.

Sm/TiCl4 system induced reductive coupling reactions: Synthesis of tetraarylfurans

Induced by low valent titanium, tetraarylfurans have been synthesized in good yields starting from aroyl chlorides under mild and neutral conditions.

Thermolysis of selenophene 1,1-dioxides

Selenophene 1,1-dioxides are thermally far labile than the corresponding thiophene 1,1-dioxides. Even heavily substituted tetraphenylselenophene 1,1-dioxide (1a) decomposed, by a process not involving cyclodimerization, when heated above its melting point or heated in refluxing toluene. Thus, the thermolysis of la in refluxing toluene afforded tetraphenylselenophene (2a, 6%), tetraphenylfuran (3a, 71%), (Z)-l,2,3,4-tetraphenyl-2-butene-l,4-dione (Z-4a, 19%), (E)-1,2,3,4-tetraphenyl-2-butene-1,4-dione (E-4a, 4%), SeO2 (23%), and Se (22%), while that of the neat sample gave 2a (5%), Z-4a (78%), E-4a (17%), SeO2 (17%), and Se (29%). Similar results were also obtained on thermolyses of a series of selenophene 1,1-dioxides. The experimental observations (influence of solvents, oxygen, and additive such as diene to the decomposition rate and the presence of induction period) revealed that the mechanism of the decomposition is highly complex. A tentative mechanism that can explain the observed products is presented.

IODOTRIMETHYLSILANE REDUCTION OF BENZOINS: SYNTHESIS OF DEOXYBENZOINS AND TETRAARYLFURANS

Benzoins react readily with idotriethylsilane to produce, in many cases, mixtures of deoxybenzoins and tetraarylfurans.