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Upstream product

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• 614-47-1 1,3-diphenyl-propen-3-one 
• 94-41-7 benzalacetophenone 
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• 29397-21-5 Diacetyldiazomethan 
• 120-46-7 1,3-diphenylpropanedione 

Relevant academic research and scientific papers

Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that CO2could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C-O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary mechanistic investigations are presented.

Rh(III)-Catalyzed Cascade Nucleophilic Addition/Annulation of 2-Diazo-1,3-diketones with 1,3-Dicarbonyl Compounds to Access 6,7-Dihydrobenzofuran-4(5 H)-ones

A Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds (e.g., 1,3-diketones and β-keto esters) is achieved to afford 6,7-dihydrobenzofuran-4(5H)-ones in up to 91% yields. Notably, a wide range of substrates and functional groups were well-tolerated under the optimized reaction conditions to give desired products in moderate to excellent yields with release of N2 and H2O as byproducts. Moreover, the method described is scalable and adaptable to late-stage functionalization.

Piano-Stool Rhodium Enalcarbenoids: Application to Catalyst-Controlled Metal-Templated Annulations of Diazoenals and 1,3-Dicarbonyls

An electrophilic piano-stool rhodium(III)-enalcarbenoid resulted from the reaction of diazoenal with the cationic CpRhIII in the presence of a 1,3-diketone. The synthetic utility of these transient carbenoids has been demonstrated in the metal-templated [3 + 2] annulation of diazoenals and 1,3-dicarbonyls, thus leading to the enal-functionalized tetrasubstituted furans. The significance of the piano-stool enalcarbenoids has been further exemplified by the mechanistically distinct, complementary Lewis acid templated [2 + 3] annulation of diazoenals and 1,3-dicarbonyls, resulting in the trisubstituted furanyl-enones and acrylates. Mechanistic investigations revealed that these annulations proceed through catalyst-dependent chemoselective activation of diazoenal by the in situ formed metal diketonates. These methodologies gave access to core structures of indeno[1,2-b]furans, tetracyclic OLED, and a pan-AKT inhibitor.

Direct CuO nanoparticle-catalyzed synthesis of poly-substituted furans: Via oxidative C-H/C-H functionalization in aqueous medium

Here, we have reported synthesis of 3,4-dicarbonyl substituted poly-functionalized furan derivatives via direct functionalization of α,β-unsaturated carbonyl compounds through conjugate addition initiated domino reactions using CuO nanoparticles as a reusable catalyst in aqueous ethanol.

Manganese dioxide-mediated oxidative coupling of 1,3-dicarbonyl compounds with α,β-unsaturated ketones: Direct access to 3,4-dicarbonyl substituted furans

An efficient manganese dioxide-mediated and highly selective oxidative C-H/C-H functionalization of 1,3-dicarbonyl compounds with α,β- unsaturated ketones for the construction of tetrasubstituted furans in one step has been demonstrated. This catalytic system converts two C-H bonds and C￡ bonds to C￡C and C-O bonds. This reaction provides a facile and regio-defined method for the synthesis of 3,4-dicarbonyl substituted furans.