1104516-50-8

Upstream product

• 501-65-5 diphenyl acetylene 
• 10488-87-6 ethyl 2-benzoylpropionate 
• 1187250-66-3 C₂₄H₁₈O₂ 
• 5337-63-3 ethyl 2-(2-phenylethyl)acetoacetate 
• 41016-29-9 2-methyl-3-phenylmaleic anhydride 
• 1199-77-5 α-methylcinnamic acid 

Downstream Products

• 59795-14-1 1-methyl-2,3,4-triphenylnaphthalene 

Relevant academic research and scientific papers

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Ruthenium(II)-Catalyzed Alkene C-H Bond Functionalization on Cinnamic Acids: A Facile Synthesis of Versatile α-Pyrones

An inexpensive ruthenium(II) complex enabled oxidative annulation of alkynes by using cinnamic acid derivatives to provide diversely decorated multisubstituted α-pyrones.

Rhodium(III)-catalysed decarbonylative coupling of maleic anhydrides with alkynes

A formal [5 - 1 + 2] annulation for the preparation of substituted α-pyrones is reported. The reaction involves the decarbonylative coupling of substituted maleic anhydrides with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II)

Rhenium- and manganese-catalyzed synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes

(Chemical Equation Presented) We have succeeded in the development of three approaches to the synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes. The first approach is a manganese-catalyzed [2+2+2] cycloaddition between 1,3-dicarbonyl compounds, which have no substituents at the active methylene moiety, and terminal alkynes. This reaction proceeds with high regioselectivity when aryl acetylenes are employed as the alkyne component. The second approach is a rhenium- or manganese-catalyzed formal [2+1+2+1] cycloaddition between β-keto esters and two kinds of alkynes. In this reaction, the aromatic compounds are obtained by the following reaction sequence: (1) insertion of the first alkyne into a carbon-carbon single bond of a β-keto ester, (2) formation of 2-pyranones via intramolecular cyclization with the elimination of ethanol, and (3) Diels-Alder reaction between the formed 2-pyranone and the second alkyne. This reaction provides multisubstituted aromatic compounds in a regioselective manner. The third approach is a rheniumcatalyzed formal [2+2+1+1] cycloaddition reaction from two 1,3-diketones and one alkyne. In this reaction, the aromatic skeleton is constructed from three carbons of the first 1,3-diketone, two carbons of the alkyne, and one carbon of the second 1,3-diketone. 2009 American Chemical Society.

Expedient synthesis of highly substituted α-pyrones from Baylis-Hillman adducts and their conversion to poly-substituted aromatics

An efficient synthetic protocol of fully substituted α-pyrones has been developed starting from the Baylis-Hillman adducts. Subsequent Diels-Alder reaction of the α-pyrones and DMAD produced poly-substituted aromatic compounds in high yields.

Rhenium- and manganese-catalyzed insertion of acetylenes into β-keto esters: Synthesis of 2-pyranones

Rhenium- and manganese-catalyzed reactions between β-keto esters and acetylenes, followed by treatment with tetrabutylammonium fluoride, gave 2-pyranone derivatives regioselectively. The Royal Society of Chemistry 2008.

Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

(Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.