Nai-Xing Wang

Synthesis of (2-Oxoindolin-3-ylidene)methyl Acetates Involving a C−H Functionalization Process

A novel palladium-catalyzed oxidative C-H functionalization protocol for the synthesis of (2-oxoindolin-3-ylidene)methyl acetates has been developed. In the presence of Pd(OAc)2 and PhI(OAc)2, a variety of N-arylpropiolamides underwent the C-H functionalization reaction with acids to afford the corresponding (E)-(2-oxoindolin-3-ylidene)methyl acetates selectively in moderate to excellent yields.

Photochemical addition reactions of [60]fullerene with 1,2-ethylenediamine and piperazine

Abstract N,N′-Dimethylethylenediamine and piperazine reacted with [60]fullerene by photoinduced-electron transfer to form the adduct compounds in a short reaction time with a good yield. NMR spectroscopy showed unambiguously that derivatives were C2v symmetric structures with a 6,6 junction, and a single-electron transfer intermediate was suggested.

Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones

A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.

Selective nickel- and manganese-catalyzed decarboxylative cross coupling of some α,β-unsaturated carboxylic acids with cyclic ethers.

A nickel- and manganese-catalyzed decarboxylative cross coupling of α, β-unsaturated carboxylic acids with cyclic ethers such as tetrahydrofuran and 1, 4-dioxane was developed. Oxyalkylation was achieved when nickel acetate was used as catalyst, while manganese acetate promoted the reaction of alkenylation.

Exploration on Asymmetric Synthesis of Flavanone Catalyzed by (S)-Pyrrolidinyl Tetrazole

An improved method of the synthesis of flavanones catalyzed by pyrrolidine and BF(3) ·Et(2) O has been developed and a lot of flavanones could be easily synthesized via this method. The asymmetric synthesis of flavanone from benzaldehyde and 5-fluoro-2-hydroxyacetophenone has been studied and flavanone with moderate enantioselectivity was obtained in one step.

[4 + 3] Cycloaddition of Aromatic α,β-Unsaturated Aldehydes and Ketones with Epoxides: One-Step Approach to Synthesize Seven-Membered Oxacycles Catalyzed by Lewis Acid

A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism for the reaction was proposed. Asymmetric reactions were proceeded and 3e was obtained with moderate ee value.

A New Type of NADH Model Compound: Synthesis and Enantioselective Reduction of Benzoylformates to the Corresponding Mandelates

A new type of NADH model compound with good reactivity and enantioselectivity has been synthesized in good yields by an efficient and convenient synthetic method. The structures of these model compounds were confirmed by 1H and 13C-NMR and MS.

Asymmetric Synthesis of Chiral Flavanone and Chromanone Derivatives

Chiral chromans and flavanones derivatives are widely exist in plants, asymmetric synthesis of biological active chiral flavanone and chromanone derivatives is a valuable research field. A chroman derivatived (+)-(S,R,R,R)-Nebivolol ( 1-adrenergic receptor blocker) has been synthesized by natural chiron and sulfoxide-directed method recently. Enantioselective method for the synthesis of flavanones and chromanones by the oxa-Michael addition and other cyclization reactions are described, asymmetric Michael-Michael cascade reaction for the construction of chiral chromans provideas a novel method in the synthesis of chiral flavanones and chromanones. Trost’s AAA reaction (Pd-catalyzed asymmetric allylic alkylation) provides a novel strategies in the synthesis of flavanones and chromanones.

Manganese-Mediated Coupling Reaction of Vinylarenes and Aliphatic Alcohols.

Alcohols and alkenes are the most abundant and commonly used organic building blocks in the large-scale chemical synthesis. Herein, this is the first time to report a novel and operationally simple coupling reaction of vinylarenes and aliphatic alcohols catalyzed by manganese in the presence of TBHP (tert-butyl hydroperoxide). This coupling reaction provides the oxyalkylated products of vinylarenes with good regioselectivity and accomplishes with the principles of step-economies. A possible reaction mechanism has also been proposed.

A new oxidation system for the oxidation of Hantzsch-1,4-dihydropyridines and polyhydroquinoline derivatives under mild conditions

A new oxidation system (Na2S2O4/TBHP) to prepare pyridine derivatives has been developed by the oxidation of 1,4-dihydropyridine derivatives and polyhydroquinoline derivatives in good to excellent yields. The procedures of the reaction were green, convenient, mild and easy work-up.