132709-17-2

Upstream product

• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 100-46-9 benzylamine 
• 492-38-6 2-phenylacrylic acid 
• 51491-68-0 2-phenylacrylyl chloride 
• 7500-45-0 N-benzylphenylacetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 529-64-6 Tropic acid 

Downstream Products

• 1233241-15-0 C₁₈H₁₉NO₃ 
• 1414882-58-8 (2E,4Z)-n-butyl 6-benzylamino-5-phenyl-6-oxohexa-2,4-dienoate 
• 1414882-82-8 (2E,4Z)-tert-butyl 6-benzylamino-5-phenyl-6-oxohexa-2,4-dienoate 

Relevant academic research and scientific papers

Small-Molecule Inhibitors Targeting Sterol 14α-Demethylase (CYP51): Synthesis, Molecular Modelling and Evaluation Against Candida albicans

Fungal infections are a global issue affecting over 150 million people worldwide annually, with 750 000 of these caused by invasive Candida infections. Azole drugs are the frontline treatment against fungal infections; however, resistance to current azole

Pd-catalyzed hydroaminocarbonylation of alkynes with aliphatic amines and its mechanism study

This work describes the hydroaminocarbonylation of alkynes with aliphatic amines without the addition of any acid additive. Excellent conversion and regioselectivity toward the formation of branched amides were obtained over a dppp-based Pd-catalytic syst

Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation

A novel chemodivergent cross-coupling of acrylamides and vinyl acetates has been realized via metal-catalyzed vinylic C-H activation. The selective olefinic C-H vinylation and alkenylation reaction was examined with a variety of differently functionalized acrylamides. The reaction efficiently generates a range of highly synthetically valuable butadienes with good functional group tolerance in good to moderate yields. A possible catalytic reaction mechanism involving the chelation-assisted olefinic C-H activation via an acetate-assisted deprotonation pathway is proposed.

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin: Via iridium-catalyzed asymmetric hydrogenation

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asymmetric catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.

Cobalt-Catalyzed Olefinic C-H Alkenylation/Alkylation Switched by Carbonyl Groups

The first cobalt-catalyzed cross-couplings between olefins has been demonstrated to provide C(alkenyl)-H alkenylation and alkylation products, using complex [Cp?Co(CO)I2]. While coupling partner acrylates afforded conjugated dienoates, α,β-unsaturated ketones led to γ-alkenyl ketones completely, representing a switchable C-H functionalization controlled by different carbonyl groups.

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

Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: Efficient access to (Z,E)-dienamides

Ruthenium- and rhodium-catalyzed direct oxidative cross-coupling reactions of acrylamides with alkenes were developed. These methods provide an efficient route for the synthesis of (Z,E)-dienamides in excellent yields with good stereoselectivity. The catalytic systems allowed oxidative olefination of a wide range of alkenes bearing different functional groups, such as CO2R, COMe, SO2Ph, aryl, CONHBn, CN, PO(OEt)2, as well as Weinreb amide.

Palladium(II)-catalyzed catalytic aminocarbonylation and alkoxycarbonylation of terminal alkynes: Regioselectivity controlled by the nucleophiles

The aminocarbonylation and alkoxycarbonylation reactions of terminal alkynes took place smoothly and efficiently using a catalyst system Pd(OAc) 2-dppb-p-TsOH-CH3CN-CO under relatively mild experimental conditions. The catalytic system was tested and optimized using two different nucleophiles: alcohols and amines. Phenylacetylene (1a) was considered as an alkyne along with diisobutylamine (2b1) andmethanol (2c1) as nucleophiles. The results showed significant differences in the conversion of 1a and in the selectivity towards the gem or trans unsaturated esters or amides with these nucleophiles. The effects of the type of palladium catalysts, the type of ligands, the amount of dppb and the solvents were carefully studied. With diisobutylamine (2b1), excellent regioselectivity towards the 2-acrylamides (gem isomer, 3ab1) was almost always observed, while trans-α,β-unsaturated esters 4ac1 was the predominant product with methanol (2c1) as a nucleophile. This remarkable sensitivity in the selectivity of the reaction indicates two different possible mechanistic pathways for these carbonylation reactions. Copyright