1507347-50-3

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 67-68-5 dimethyl sulfoxide 
• 578-66-5 8-amino quinoline 
• 492-38-6 2-phenylacrylic acid 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 51491-68-0 2-phenylacrylyl chloride 

Downstream Products

• 212315-75-8 methyl (Z)-3-iodo-2-phenyl-2-propenoate 
• 137420-62-3 (Z)-methyl 2-phenyl-3-(p-tolyl)acrylate 

Relevant academic research and scientific papers

Lewis acid-promoted cascade reaction for the synthesis of Michael acceptors and its application in a dimerization reaction

An efficient Lewis acid-promoted cascade reaction with dimethyl sulfoxide as a methylene source for the synthesis of Michael acceptors is reported. The key to developing this procedure is the selection of a mild base to modulate the equilibrium of various intermediates in order to drive the reaction forward to the formation of Michael acceptor and dimeric compound products. Extensive studies were performed to gain insight into a possible reaction mechanism.

Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach

In this study, a general approach towards the synthesis of trifluoromethylthiolated olefinic and aromatic compounds was developed. Under Pd-catalysis, the direct introduction of a SCF3 group was realized in the presence of the Munavalli reagent as the electrophilic SCF3 source and in the absence of additives. A large number of acrylamides and aromatic amides derived from 8-aminoquinoline and 5-methoxy-aminoquinoline were functionalized in moderate to high yields (up to 89 %). The cleavage of the directing groups was smoothly achieved, demonstrating further the synthetic utility of the present approach and offering a straightforward access to various original SCF3-containing molecules.

Pd-Catalyzed Selective Chlorination of Acrylamides at Room Temperature

In this Letter, the transition-metal-catalyzed chlorination of alkenes is reported. In the presence of the commercially available and inexpensive N-chlorosuccinimide and without additive, the Pd-catalyzed chlorination of acrylamides by C-H bond activation was developed at room temperature under air. Under these mild reaction conditions, the versatility of the methodology was demonstrated as an array of acrylamides was functionalized to selectively provide the corresponding difficult-to-synthesize chlorinated olefins as a single Z stereoisomer. Mechanistic studies were conducted to get insights into the reaction mechanism, and post-functionalization reactions further demonstrated the synthetic utility of the approach toward the access to high value-added chlorinated compounds.

Direct Csp3-H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source

A direct Csp3-H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source was developed. The formyl group of DMF delivered the carbon and one hydrogen atoms, and the Me2NH-BH3 dona

Preparation method of 2-aminotetralin derivative and intermediates thereof

The invention relates to a preparation method of a 2-aminotetralin derivative and intermediates thereof. According to the method, a core framework of the 2-aminotetralin derivative can be synthesized,and precursor molecules of medicine molecules U93385 an

Access to Isothiazolones from Simple Acrylamides by Pd-Catalyzed C-H Bond Activation

A new methodology was developed to access isothiazolone derivatives from simple acrylamides by transition metal catalyzed C-H bond functionalization. This Pd-catalyzed reaction using an electrophilic SCN source offered an efficient tool to access a panel of functionalized isothiazolone derivatives (21 examples, up to 71% yield).

Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids

We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.

Pd-catalyzed diastereoselective trifluoromethylthiolation of functionalized acrylamides

The Pd-catalyzed diastereoselective trifluoromethylthiolation of acrylamides was developed to allow the formation of the Z-isomer as a single product. Using a C-H bond functionalization strategy, the method was applied to a broad range of α-aryl, α-alkyl, and α, β-disubstituted acrylamides bearing the amide derived from the 8-aminoquinoline as a directing group. Mechanistic studies as well as postfunctionalization of the products were performed. This approach opens new routes to unprecedented SCF3-containing scaffolds.

Stereoselective synthesis of Z-vinylsilanes via palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds

An efficient and convenient palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.

Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization

A palladium-catalyzed C-H bond functionalization of acrylamides was developed to build up stereoselectively trifluoromethylated 1,3-butadienes. Using a tertiary amide as a directing group, olefins were selectively functionalized with 2-bromo-3,3,3-trifluoropropene to access these important fluorinated compounds. The methodology was extended to the construction of pentafluoroethyl-substituted 1,3-dienes. Mechanistic studies supported by density functional theory calculations suggested a redox neutral mechanism for this transformation.