Yun-Yang Wei

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Organization: Nanjing University of Science and Technology

Department: School of Chemical Engineering

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TOPICS

Organic Chemistry

Hypervalent Iodine

Chemicals
References

Copper catalyzed direct alkenylation of simple alkanes with styrenes

Co-reporter:Yefeng Zhu and Yunyang Wei

Chemical Science 2014 vol. 5(Issue 6) pp:2379-2382

Publication Date(Web):21 Feb 2014

DOI:10.1039/C4SC00093E

A novel Cu-catalyzed direct alkenylation of simple alkanes with styrenes was described. In the presence of a catalytic amount of Cu(OTf)2, a diverse range of alkenes undergo coupling with cycloalkanes to produce (E)-alkyl alkenes. This transformation is proposed to proceed via a radical process.

Design and Synthesis of 3-Trifluoromethyl-3H-pyrazoles and Further Investigations of Their Transformation to 1H-Pyrazoles

Co-reporter:Qiang Sha;Haixuan Liu;Yunyang Wei

European Journal of Organic Chemistry 2014 Volume 2014( Issue 34) pp:7707-7715

Publication Date(Web):

DOI:10.1002/ejoc.201403141

Abstract

An efficient intramolecular cycloaddition strategy for the synthesis of trifluoromethyl-substituted 3H-pyrazoles was developed. Subsequently, their wide applications were demonstrated: they (1) react with dioxane by a radical process and (2) undergo [1,5] sigmatropic rearrangements. These applications are useful as the products were obtained in high yields and with excellent regioselectivity.

Copper(I)-Catalyzed Wittig Olefination Reactions of N-Tosylhydrazones with Trifluoromethylketones

Co-reporter:Dr. Qiang Sha ; Yunyang Wei

ChemCatChem 2014 Volume 6( Issue 1) pp:131-134

Publication Date(Web):

DOI:10.1002/cctc.201300583

Abstract

Cuprous iodide-catalyzed Wittig olefination reactions of N-tosylhydrazones with trifluoromethylketones are reported. This procedure provides an efficient method for the synthesis of various trifluoromethyl-substituted alkenes in moderate to good yields (up to 89 % yield) and good stereoselectivity (up to 93 % E-selectivity). To the best of our knowledge, it is the first report of a Wittig reaction of N-tosylhydrazones with ketones.

Hypervalent Iodine(III)-Mediated Benzannulation of Enamines with Alkynes for the Synthesis of Polysubstituted Naphthalene Derivatives

Co-reporter:Peng Gao, Jinjian Liu, and Yunyang Wei

Organic Letters 2013 Volume 15(Issue 11) pp:2872-2875

Publication Date(Web):May 15, 2013

DOI:10.1021/ol401206g

A series of functionalized 1-amino-2-naphthalenecarboxylic acid derivatives were synthesized from enamines and alkynes via a benzannulation strategy mediated by iodosylbenzene and BF3·Et2O. The advantages of this novel benzannulation process include broad substrate scope, good functional group tolerance, and mild reaction conditions without the use of heavy metals.

Capture of In Situ Generated Diazo Compounds or Copper Carbenoids by Triphenylphosphine: Selective Synthesis of trans- Alkenes and Unsymmetric Azines via Reaction of Aldehydes with Ketone-Derived N-Tosylhydrazones

Co-reporter:Qiang Sha;Yifei Ling;Wenyong Wang ;Yunyang Wei

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 11-12) pp:2145-2150

Publication Date(Web):

DOI:10.1002/adsc.201300302

One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines

Co-reporter:Qiang Sha and Yun-Yang Wei

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 34) pp:5615-5620

Publication Date(Web):25 Jun 2013

DOI:10.1039/C3OB40745D

A new, convenient and efficient transition metal-free synthesis of S-alkyl dithiocarbamates through one-pot reaction of N-tosylhydrazones, carbon disulfide and amines is reported. Tosylhydrazones derived from various aromatic and aliphatic ketones or aldehydes were tested and gave dithiocarbamates in good to excellent yields. The tosylhydrazones can be generated in situ without isolation, which provides a simpler one-pot method to synthesize dithiocarbamates via the reaction of carbonyl compounds, carbon disulfide and amines in the presence of 4-methylbenzenesulfonohydrazide.

Solvent-Controlled Copper-Catalyzed Oxidation of Benzylic Alcohols to Aldehydes and Esters

Co-reporter:Yefeng Zhu ;Yunyang Wei

European Journal of Organic Chemistry 2013 Volume 2013( Issue 21) pp:4503-4508

Publication Date(Web):

DOI:10.1002/ejoc.201300668

Abstract

A procedure for the copper-catalyzed selective oxidation of primary alcohols to esters and aldehydes was developed. Under solvent-free conditions, self-oxidative esterification and cross-esterification of benzyl alcohols with various aliphatic alcohols proceed smoothly to give the corresponding esters in good yields. If DMF was used as a solvent, the benzyl alcohols were selectively converted into the corresponding aldehydes in excellent yields.

Aerobic Multicomponent Tandem Synthesis of 3-Sulfenylimidazo[1,2-a]pyridines from Ketones, 2-Aminopyridines, and Disulfides

Co-reporter:Wenlei Ge;Xun Zhu;Yunyang Wei

European Journal of Organic Chemistry 2013 Volume 2013( Issue 27) pp:6015-6020

Publication Date(Web):

DOI:10.1002/ejoc.201300905

Abstract

An aerobic CeCl₃·7H₂O/NaI-catalyzed C–H functionalization reaction was developed for the synthesis of 3-sulfenylimidazo[1,2-a]pyridines from easily available ketones, 2-aminopyridines, and disulfides without DMSO or peroxide as an oxidant. This three-component tandem reaction process involves the formation of imidazo[1,2-a]pyridines followed by Friedel–Crafts sulfenylation in one pot under mild conditions. Both aryl and alkyl ketones afforded the desired products in good to excellent yields without the presence of other additives.

Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides: efficient synthesis of esters of tertiary alcohols

Co-reporter:Yefeng Zhu and Yunyang Wei

RSC Advances 2013 vol. 3(Issue 33) pp:13668-13670

Publication Date(Web):24 Jun 2013

DOI:10.1039/C3RA40246K

Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides has been developed. This protocol affords a novel approach for the synthesis of carboxylic esters of tertiary alcohols under mild conditions. Depending on the catalyst system, a variety of tertiary esters were produced in good to excellent yields.

Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate

Co-reporter:Wenlei Ge, Xun Zhu and Yunyang Wei

RSC Advances 2013 vol. 3(Issue 27) pp:10817-10822

Publication Date(Web):19 Apr 2013

DOI:10.1039/C3RA40872H

The iodine catalyzed one-pot two-step oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant has been achieved, providing a convenient and efficient method for the synthesis of quinazolinones in good to excellent yields via in situ oxidation of primary alcohols to aldehydes. The reaction was carried out in the green solvent DMC, under atmospheric conditions. The procedure is suitable for aromatic or alkyl primary alcohols.

Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene

Co-reporter:Haixuan Liu, Yunyang Wei

Tetrahedron Letters 2013 Volume 54(Issue 35) pp:4645-4648

Publication Date(Web):28 August 2013

DOI:10.1016/j.tetlet.2013.06.053

A mild and efficient protocol for the construction of 1,4-dihydro-3,6-disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good to excellent yields. The corresponding 3,6-disubstituted-1,2,4,5-tetrazines can be easily obtained through one-step N-deprotection of p-toluensulfonyl groups and aromatization by tetrabutyl ammonium fluoride in THF. A mechanism has been proposed.

Base and solvent mediated decomposition of tosylhydrazones: highly selective synthesis of N-alkyl substituted hydrazones, dialkylidenehydrazines, and oximes

Co-reporter:Qiang Sha, Yunyang Wei

Tetrahedron 2013 69(19) pp: 3829-3835

Publication Date(Web):

DOI:10.1016/j.tet.2013.03.055

Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate

Co-reporter:Wenlei Ge and Yunyang Wei

Green Chemistry 2012 vol. 14(Issue 7) pp:2066-2070

Publication Date(Web):11 May 2012

DOI:10.1039/C2GC35337G

The iodine catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant has been achieved under ambient conditions, providing a convenient and efficient method for the synthesis of 3-sulfenylindoles in good to excellent yields and with high selectivity. The reaction was carried out in a green solvent, DMC, under atmospheric conditions. Only 0.5 mmol of disulfide was needed for the 3-sulfenylation of 1 mmol of indole because both the sulfenyl groups of a symmetric disulfide take part in the reaction. The procedure is suitable for N-protected or unprotected indoles.

Facile Preparation and Reactivity of Magnetic Nanoparticle- Supported Hypervalent Iodine Reagent: A Convenient Recyclable Reagent for Oxidation

Co-reporter:Chenjie Zhu ;Yunyang Wei

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 2-3) pp:313-320

Publication Date(Web):

DOI:10.1002/adsc.201100601

Abstract

A simple three-step preparation of magnetic nanoparticle-supported (diacetoxyiodo)benzene starting from 4-iodobenzoic acid is described. The nanoparticle reagent was obtained with good loading levels and has been successfully used for efficient oxidation of a wide range of alcohols. The supported reagent demonstrated comparable activity with that of its homogeneous counterpart (diacetoxyiodo)benzene and could be simply recycled with the assistance of an external magnet.

A Simple and Highly Selective Biomimetic Oxidation of Alcohols with Hypervalent Iodine(III) Reagent Catalyzed by β-Cyclodextrin in Water

Co-reporter:Chenjie Zhu;Yunyang Wei

Catalysis Letters 2011 Volume 141( Issue 4) pp:582-586

Publication Date(Web):2011 April

DOI:10.1007/s10562-011-0545-y

A simple, mild and highly efficient biomimetic oxidation of alcohols to the corresponding aldehydes or ketones with hypervalent iodine(III) reagent catalyzed by β-cyclodextrin was reported. β-cyclodextrin serves as a biological catalyst to enhance the reaction remarkably. The oxidation proceeded in water to afford aldehydes or ketones in excellent yields and high selectivity without remarkable over-oxidation to carboxylic acids. Selective oxidation of primary alcohols in the presence of secondary alcohols was also achieved. A possible mechanism for the oxidation was proposed.

An Inorganic Iodine-Catalyzed Oxidative System for the Synthesis of Benzimidazoles Using Hydrogen Peroxide under Ambient Conditions

Co-reporter:Chenjie Zhu ; Yunyang Wei

ChemSusChem 2011 Volume 4( Issue 8) pp:1082-1086

Publication Date(Web):

DOI:10.1002/cssc.201100228

Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water

Co-reporter:Yefeng Zhu;Yixing Shi;Yunyang Wei

Monatshefte für Chemie - Chemical Monthly 2010 Volume 141( Issue 9) pp:1009-1013

Publication Date(Web):2010 September

DOI:10.1007/s00706-010-0363-8

1,4-Bis(2-hydroxy-5-methoxybenzyl)piperazine and its analogues were used as efficient ligands for CuI-catalyzed N-arylation of imidazoles with aryl halides in water under mild conditions (120 °C for 12 h) with 10 mol% of CuI, 20 mol% of the Mannich base, and two equivalents of KOH or K2CO3 in the presence of 10 mol% phase transfer catalyst (n-Bu)4NBr. A variety of products were synthesized in moderate to excellent yields using this inexpensive catalytic system.

Catalytic hypervalent iodine oxidation of alcohols to corresponding aldehydes or ketones using 2,2,6,6-tetramethylpiperidinyl-1-oxy and potassium peroxodisulfate

Co-reporter:Chenjie Zhu;Lei Ji;Yunyang Wei

Monatshefte für Chemie - Chemical Monthly 2010 Volume 141( Issue 3) pp:327-331

Publication Date(Web):2010 March

DOI:10.1007/s00706-010-0260-1

An efficient, facile, and mild oxidation of alcohols to the corresponding aldehydes or ketones with potassium peroxodisulfate and 2,2,6,6-tetramethylpiperidinyl-1-oxy in the presence of a catalytic amount of iodobenzene is reported. The oxidation proceeded in a mixed solvent to afford carbonyl compounds in moderate to excellent yields. A possible mechanism for the oxidation is proposed.

Molecular sieve promoted copper catalyzed aerobic oxidation of alcohols to corresponding aldehydes or ketones

Co-reporter:Liu Lin, Ma Juanjuan, Ji Liuyan, Wei Yunyang

Journal of Molecular Catalysis A: Chemical 2008 Volume 291(1–2) pp:1-4

Publication Date(Web):29 August 2008

DOI:10.1016/j.molcata.2008.06.001

A novel combination of catalyst system of CuCl/TEMPO-IL/MS3A, which catalyzed the aerobic oxidation of alcohols in ionic liquid [bmim][PF6] into aldehydes or ketones in high yields and selectivity, was reported. Molecular sieve 3A was found to have a significant beneficial effect on the catalytic reactions. The beneficial effect of Molecular sieve 3A was attributed to its Brønsted base property. With TEMPO being immobilized on ionic liquid to form TEMPO-IL and the use of a heterogeneous promoter of MS3A, the catalyst system could easily be recycled and reused without loss in catalytic activity.An efficient and selective aerobic oxidation procedure of alcohols to the corresponding aldehydes or ketones using CuCl/TEMPO-IL/MS3A catalytic system in ionic liquid [bmim][PF6] has been developed. MS3A serves as a heterogeneous Brønsted base to enhance the reaction rate remarkably. It is noteworthy to mention that the catalysts and solvent could easily be recycled and reused without loss of activity.

Aerobic selective oxidation of alcohols to aldehydes or ketones catalyzed by ionic liquid immobilized TEMPO under solvent-free conditions

Co-reporter:Lin Liu;Liu-Yan Ji

Monatshefte für Chemie - Chemical Monthly 2008 Volume 139( Issue 8) pp:901-903

Publication Date(Web):2008 August

DOI:10.1007/s00706-008-0861-0

A selective ionic-liquid immobilized TEMPO/CuCl catalyzed oxidation procedure of alcohols to the corresponding aldehydes and ketones with molecular oxygen under solvent-free conditions was developed. The catalyst was easily recovered and reused in the reaction.

Synthesis and Analgesic Activities of Endomorphin-2 and Its Analogues

Co-reporter:Yun-Yang Wei;Zhi-Hao Shi;Li Yu;Chuan-Jin Wang

Chemistry & Biodiversity 2007 Volume 4(Issue 3) pp:458-467

Publication Date(Web):19 MAR 2007

DOI:10.1002/cbdv.200790038

Endomorphin-2 (1; H-Tyr-Pro-Phe-Phe-NH₂; EM2) and its novel cyclic asparagine (cycloAsn) analogues, H-Tyr-cAsn(CHPh)-Phe-Phe-NH₂ (2) and H-Tyr-cAsn(CHMe₂)-Phe-Phe-NH₂ (3), were synthesized via liquid-phase synthesis. The structures of the products and intermediates were characterized by IR, ¹H-NMR, MS, and HR-MS analyses. The antinociceptive activity of EM2 and its cyclic asparagine analogues were assessed in AcOH-induced abdominal constriction tests in mice with i.p. injection. The results show that the antinociceptive activities of EM2 and its cyclic asparagine analogue 2 were higher than those of aspirine and meperidine. Analogue 2 was observed to be a stronger analgesic with dose-dependence than EM2. The test mice did not show any tendency to be addicted while administrated of analogue 2 repeatedly and regularly.

Clean and selective oxidation of alcohols with n-Bu4NHSO5 catalyzed by ionic liquid immobilized TEMPO in ionic liquid [bmim][PF6]

Co-reporter:Chenjie Zhu, Lei Ji, Yunyang Wei

Catalysis Communications (1 July 2010) Volume 11(Issue 12) pp:1017-1020

Publication Date(Web):1 July 2010

DOI:10.1016/j.catcom.2010.05.002

An efficient oxidation of alcohols with tetra-n-butylammonium peroxymonosulfate catalyzed by ionic liquid immobilized TEMPO in ionic liquid [bmim][PF6] was reported. TEMPO-IL serves as a homogeneous catalyst to enhance the reaction remarkably. The oxidation proceeded to afford aldehydes or ketones in excellent yields and high selectivity without remarkable over-oxidation to carboxylic acids. It is noteworthy to mention that the catalyst and solvent could easily be recycled and reused without loss of activity. A possible mechanism for the oxidation is proposed.

Copper catalyzed direct alkenylation of simple alkanes with styrenes

Co-reporter:Yefeng Zhu and Yunyang Wei

Chemical Science (2010-Present) 2014 - vol. 5(Issue 6) pp:NaN2382-2382

Publication Date(Web):2014/02/21

DOI:10.1039/C4SC00093E

One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines

Co-reporter:Qiang Sha and Yun-Yang Wei

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 34) pp:NaN5620-5620

Publication Date(Web):2013/06/25

DOI:10.1039/C3OB40745D