Zhi-Zhen Huang

Tandem reaction of α-hypervalent iodo functionalized phosphonium and arsonium ylides as umpolung reagents

α-Hypervalent iodo functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give α-heteroatom substituted ylides 4 in good yields. A tandem sequence of nucleophilic substitution then Wittig reaction occurs smoothly to form (Z)-α-halo-α,β-unsaturated esters 6, stereoselectively, in moderate to excellent yields.

Morita–Baylis–Hillman Reaction of α,β-Unsaturated Ketones with Allylic Acetates by the Combination of Transition-Metal Catalysis and Organomediation

An intermolecular Morita-Baylis-Hillman (MBH) reaction of α,β-unsaturated ketones with allylic acetates under the catalysis of 10 mol % of tetrakis(triphenylphosphine)palladium(0) and mediation of tributylphosphine has been developed in the presence of acetic acid, affording the desired α-coupling products. The MBH reaction has the advantages of good tolerance to many functional groups, excellent regioselectivity and E-stereoselectivity, and moderate to good yields.

A FACILE SYNTHESIS OF α-PHENYLSELENO-α,β-UNSATURATED NITRILES VIA α-PHENYLSELENENYL CYANOMETHYLENE TRIPHENYLARSORANE

ABSTRACT α-Phenylseleno-α,β-unsaturated nitriles can be synthesized smoothly via α-phenylselenenyl cyanomethylene triphenylarsorane in good yields.

Stereoselective Synthesis of α-Bromo-α,β-unsaturated Ketones via Wittig Reaction

Abstract The synthesis of α-bromo benzoylmethylene triphenylphosphorane 2 is firstly reported and α-bromo ylide 2 has sufficient activity to undergo Wittig reaction, affording a novel method for the stereoselective synthesis of α-bromo-α,β-unsaturated ketones 5.

Synthesis of α-Phenylthioacylmethylene Triphenylarsoranes and their Wittig-type Reactions

α-Phenylthio acylmethylene triphenylarsoranes, the first stable α-thiyl arsonium ylides, are prepared by phenylsulfenylation–transylidation reaction of the corresponding acylmethylene triphenylarsoranes with phenylsulfenyl chloride; Wittig reactions are carried out under mild reaction conditions on the arsonium ylides to provide α-phenylthio-α,β-unsaturated ketones.

First application of ionic liquid to reactions involving organotellurium compounds as intermediates

The condensation reaction of telluronium salts 1 with aldehydes and dibutyl telluride 4, bromide 5 with aldehyde 2 proceeded smoothly in the ionic solvent [bmim][BF4], affording a novel method for the stereoselective synthesis of (E)-α,β-unsaturated compounds 3 in high purity, excellent yields and high stereoselectivity.

Novel stereoselective synthesis of (E)-α,β-unsaturated nitriles and ketones by the tandem reaction of deprotonation-oxidation-Wittig reaction from phosphonium salts

Phosphonium salt 1 and the alcohol 2 can undergo a tandem deprotonation–oxidation–Wittig reaction in the presence of sodium hydroxide and manganese dioxide, afford to an efficient method for the stereoselective synthesis of (E)-α,β-unsaturated nitriles and ketones 3.

Highly stereoselective synthesis of trans-diaryl epoxides via semi-stabilised telluronium ylide

Benzyldibutyltelluronium bromide can react with LDA to form benzyldibutyltelluronium ylide in situ , followed by the reaction with aromatic aldehydes, developed a novel method for the stereoselective synthesis of trans -diaryl epoxides.

THE BARBIER REACTION OF 1-CHLOROMETHYLBENZO- TRIAZOLE WITH IMINES AND SUCCESSIVE ELIMINATION

ABSTRACT Under the mediation of samarium diiodide, 1-chloromethyl-benzotriazole 1 can undergo Barbier reaction smoothly with imines 2 to produce 1-(β-aminoethyl)benzotriazole 3. Successive elimination of 3 gives imines 7 increased one carbon. The possible mechanism is proposed as well.

Direct Synthesis of α-Acyl Methylenetriphenylarsoranes from Readily Available Arsonium Salts

Abstract α-Acyl arsoranes can be synthesized by the acylation of readily available salts in the presence of triethylamine in moderate to good yields.