143952-59-4

Upstream product

• 619-44-3 methyl 4-iodobenzoate 
• 623-47-2 propynoic acid ethyl ester 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 1539299-77-8 (Z)-methyl 4-(1-chloro-3-ethoxy-3-oxo-2-((2-oxotetrahydrofuran-3-yl)methyl)prop-1-en-1-yl)benzoate 
• 1582221-68-8 ethyl 5-(4-(methoxycarbonyl)phenyl)-2-phenyloxazole-4-carboxylate 
• 1638667-68-1 (Z)-methyl 4-(1-chloro-3-ethoxy-3-oxo-2-((4-oxooxetan-2-yl)methyl)prop-1-en-1-yl)benzoate 
• 90998-43-9 methyl 4-(3-ethoxy-3-oxoprop-1-en-1-yl)benzoate 
• 1564265-62-8 methyl 4-(3,4-bis(2,4-dimethylphenyl)-2-(ethoxycarbonyl)-5-oxocyclopenta-1,3-dien-1-yl)benzoate 

Relevant academic research and scientific papers

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Palladium-Catalyzed Regio- and Stereoselective Sulfonylation of Aryl Propiolates with Sulfonyl Hydrazides: Access to (E)-β-Aryl Sulfonyl Acrylates

An efficient method for the synthesis of (E)-β-aryl sulfonyl acrylates has been reported. This palladium-catalyzed approach showed excellent regio- and stereoselectivity in the sulfonylation of aryl propiolates with sulfonyl hydrazides. Through this approach, a wide range of (E)-β-aryl sulfonyl acrylates were obtained in moderate to high yields. (Figure presented.).

Trans -Hydroboration vs. 1,2-reduction: Divergent reactivity of ynones and ynoates in Lewis-base-catalyzed reactions with pinacolborane

Ynones and ynoates react with pinacolborane in a divergent manner in the presence of nucleophilic phosphine catalysts. Ynones are transformed to the corresponding propargyl alcohols in good yields with high regio- and chemoselectivity. Ynoates undergo highly regio- and stereoselective trans-hydroboration to produce E-vinylboronates. Impressive divergence in reactivity of ynones and ynoates can be traced back to the mechanistic aspects of 1,2-reduction and trans-hydroboration. A comparative analysis of the two pathways paints a complex picture in which different reaction rates control selectivity in these seemingly unrelated processes and explains how sufficiently acidic protons in the reaction mixtures can be used to steer the selectivity in different directions.

A convenient regioselective synthesis of cyclopentadienones via palladium-catalyzed [2+2+1] cyclocarbonylation of alkynes

A simple and efficient synthesis of cyclopentadienones via palladium-catalyzed cyclocarbonylation of alkynes under atmospheric pressure of carbon monoxide has been developed. The transformation was carried out under mild and ligand-free conditions, a wide range of substrates and exceptional functional group tolerance.

Ligand-free copper(Ι)-catalyzed Sonogashira-type coupling of arylboronic acids with terminal alkynes

An efficient ligand-free CuI-catalyzed Sonogashira-type coupling reaction of arylboronic acids with terminal alkynes under air is described. The electron-deficient alkynes gave the desired cross-coupling products in good yields. Thus, it represents a simple and alternative method for the traditional Sonogashira reaction.

Preparation of ethyl arylpropiolates from aryl iodides by palladium-catalyzed cross-coupling reaction

The palladium-catalyzed cross-coupling reaction of aryl iodides with 3,3,3-triethoxy-1-propyne gave 1-aryl-3,3,3-triethoxy-1-propynes which were converted to the corresponding ethyl arylpropiolates. The arylpropiolates were also synthesized from the cross-coupling reactions of aryl iodides with 2-ethoxycarbonyl-1-ethynylzinc chloride or ethyl (tributylstannyl)propiolate, but the reactions were not generally applicable.