76457-91-5

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 122-51-0 orthoformic acid triethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 1122-91-4 4-bromo-benzaldehyde 
• 589-87-7 1,4-bromoiodobenzene 
• 107-19-7 propargyl alcohol 
• 37614-58-7 3-(4-bromophenyl)prop-2-yn-1-ol 

Downstream Products

• 1022915-12-3 1-phenyl-N-[3-(4-bromophenyl)prop-2-ynylidene]methanamine oxide 
• 1203668-61-4 (E)-1-bromo-4-(4-nitrobut-3-en-1-ynyl)benzene 
• 1241601-86-4 (E)-3-(4-bromophenyl)-1-(2-styrylphenyl)prop-2-yn-1-ol 
• 1254213-05-2 (R) ethyl 2-(4-bromophenyl)-3-formy-4-hydroxy-4H-chromene-4-carboxylate 
• 1254213-04-1 (R) ethyl 2-(4-bromophenyl)-3-formy-4-hydroxy-6-methyl-4H-chromene-4-carboxylate 
• 1254213-03-0 (R) ethyl 2-(4-bromophenyl)-3-formy-4-hydroxy-7-methoxy-4H-chromene-4-carboxylate 
• 1261120-07-3 ethyl 4-(4-bromophenyl)-6-methyl-2-oxo-3,4-dihydro-2H-pyran-5-carboxylate 
• 1301185-55-6 C₁₀H₆BrNO 

Relevant academic research and scientific papers

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.

Organocatalytic Regio- and Enantioselective N-Alkylation of Isoxazol-5-ones

A chiral phosphoric acid catalyzed regio- and enantioselective reaction between 1-acylamino-3-arylprop-2-yn-1-ols and isoxazol-5-ones has been developed for the first time. With the established protocol, N-alkylation of isoxazol-5-ones was achieved, affording enantioenriched N,N-acetals in 74–99 % yield with 72–88 % ee.

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application

The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.

Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.

Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization

A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Gold-Catalyzed Synthesis of 2,5-Disubstituted Oxazoles from Carboxamides and Propynals

2,5-Disubstituted oxazoles are synthesized by oxidative gold catalysis. In contrast to a reported procedure that delivers 2,4-disubstituted oxazoles starting from terminal alkynes, a switch in selectivity towards a 2,5-disubstitution is achieved by the use of propynals as starting materials. In the new reaction, the key intermediate is formed by the nucleophilic attack of the carboxamide onto a gold carbenoid, and then condensates with the more electrophilic aldehyde moiety already present in the substrate and not with the ketone that is derived from the oxygen donor. This new cyclization mode introduces a new carbonyl moiety as substituent at the 2,5-disubstituted oxazole, an attractive motive that can be found in bioactive compounds or be used for further derivatizations. (Figure presented.).

Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes

A copper-catalyzed silylation of propargyl dichlorides was developed to access chloro-substituted allenylsilanes under mild reaction conditions. Moreover, enantioenriched chloro-substituted allenylsilanes can be synthesized in moderate to high yields and good enantioselectivities with this protocol.

Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles to Construct a Pyrrole Core

This work reports gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles or benzisoxazoles to yield pyrrole derivatives. The reaction chemoselectivity is controlled by an initial attack of an isoxazole at a less hindered alkyne to form gold carbenes, further inducing a 1,2-migration of a second alkyne group. A broad substrate scope of 1,4-diyn-3-ols, isoxazoles and even benzisoxazoles highlighted the reaction utility.