62358-86-5

Upstream product

• 10160-87-9 Propiolaldehyde diethyl acetal 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 122-51-0 orthoformic acid triethyl ester 
• 766-97-2 4-n-methylphenylacetylene 
• 1620152-57-9 2,2-diethoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole 
• 20461-86-3 2,2-diethoxy acetic acid 
• 33491-05-3 1-(2-bromoethynyl)-4-methylbenzene 

Downstream Products

• 73057-40-6 3-(4-methylphenyl)prop-2-ynal 
• 181420-37-1 (Z)-3,3-diethoxy-2-(p-methoxyphenyl)-1-(p-methylphenyl)-1-propene 
• 1071059-06-7 1-Phenyl-9-((E)-4-p-tolyl-but-1-en-3-ynyl)-phenanthrene 
• 73057-46-2 1-Phenyl-12-p-tolyl-triphenylene 

Relevant academic research and scientific papers

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.

Blue light photoredox-catalysed acetalation of alkynyl bromides

Herein, we report an organo-photoredox-based protocol using 2,2-diethoxyacetic acid as the acetal source to achieve acetalation of alkynyl bromides to afford various alkynyl acetal products. In addition to arylethynyl bromides, substrates bearing heteroaryl rings (thiophene, pyridine, and indole) smoothly gave the corresponding acetalation products. This mild protocol has potential utility for the synthesis of aldehydes by further protonization.

CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: A general method for the synthesis of unsymmetrical propargylic acetals

A general source of dialkoxycarbenes, 2,2-dialkoxy-5,5-dimethyl- Δ3-1,3,4-oxadiazolines, have been successfully employed as coupling partners in CuI-catalyzed cross-coupling reactions with terminal alkynes, which afforded various unsymmetrical propargylic acetals in good yields. This journal is the Partner Organisations 2014.

Synthesis of 1,5-disubstituted (E)-pent-2-en-4-yn-1-ones

The condensation of 3-arylpropynals with aryl methyl ketones in the presence of sodium hydroxide in 50% aqueous ethanol at 0°C (Claisen-Schmidt reaction) afforded up to 89% of the corresponding (E)-1,5-diarylpent-2-en-4-yn- 1-ones. The E configuration of the double C=C bond and cis conformation of the enone fragment in the products in crystal and CDCl3 solution were determined by X-ray analysis and 1H NMR spectroscopy.

Sonogashira reaction of aryl halides with propiolaldehyde diethyl acetal catalyzed by a tetraphosphine/palladium complex

All-cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 efficiently catalyzes the Sonogashira reaction of propiolaldehyde diethyl acetal with a variety of aryl bromides and chlorides. A minor electronic effect of the substituents of the aryl bromide was observed. Similar reaction rates were observed in the presence of activated aryl bromides such as 4-trifluoromethylbromobenzene and deactivated aryl bromides such as bromoanisole. Turnover numbers up to 95,000 can be obtained for this reaction. Even aryl chlorides and heteroarylbromides or chlorides have been successfully alkynylated with this catalyst. Moreover, a wide variety of substituents on the aryl halide such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, nitro, dimethylamino or nitrile are tolerated.

Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines

Acetylenic acetals and ketals have been reacted with aryl and vinyl halides to generate hydroarylation and hydrovinylation products. The reaction proceeds with high regioselectivity. The carbopalladation step appears to be mainly controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon bearing the acetal group. The reaction has been employed to develop a regioselective synthesis of 3-aryl and 3-vinylquinolines.