Hui-jun Zhang

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Organization: Xiamen University

Department: Department of Chemistry, College of Chemistry and Chemical Engineering

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TOPICS

Organic Chemistry

C-H Activation

Chemicals
References

Direct Synthesis of Large-Scale Ortho-Iodinated Perylene Diimides: Key Precursors for Functional Dyes

Co-reporter:Jiajun Wu, Dezhi He, Li Zhang, Yudong Liu, Xiaogang Mo, Jianbin Lin, and Hui-jun Zhang

Organic Letters October 6, 2017 Volume 19(Issue 19) pp:

Publication Date(Web):September 28, 2017

DOI:10.1021/acs.orglett.7b02718

A highly regioselective tetra-ortho-iodination reaction of perylene diimides (PDIs) has been developed, which could be conducted on a multigram scale (>10 g), featuring a column chromatography-free workup and purification. The ortho-iodinated-PDIs serve as key intermediates for the preparation of a variety of ortho-functionalized PDIs and PDI-based conjugated polymers.

Rhodium-Catalyzed β-Selective Oxidative Heck-Type Coupling of Vinyl Acetate via C–H Activation

Co-reporter:Hui-Jun ZhangWeidong Lin, Feng Su, Ting-Bin Wen

Organic Letters 2016 Volume 18(Issue 24) pp:6356-6359

Publication Date(Web):December 2, 2016

DOI:10.1021/acs.orglett.6b03244

An efficient Rh(III)-catalyzed direct ortho-C–H olefination of acetanilides with vinyl acetate was developed. This protocol provides a straightforward pathway to a series of (E)-2-acetamidostyryl acetates, giving access to indole derivatives following a simple hydrolysis/cyclization process.

2,5,8,11-Tetraalkenyl Perylene Bisimides: Direct Regioselective Synthesis and Enhanced π–π Stacking Interaction

Co-reporter:Li Zhang, Dezhi He, Yudong Liu, Kun Wang, Zongxia Guo, Jianbin Lin, and Hui-Jun Zhang

Organic Letters 2016 Volume 18(Issue 22) pp:5908-5911

Publication Date(Web):November 10, 2016

DOI:10.1021/acs.orglett.6b03012

A series of 2,5,8,11-tetraalkenyl perylene bisimide (PBI) derivatives were synthesized through Ru(II)- or Rh(III)-catalyzed regio- and steroselective oxidative C–H olefination in one step. The optical electronic and self-assembly of the 2,5,8,11-substituted PBIs were investigated, which showed great potential in optoelectronic applications.

Synthesis of α-Aminonaphthalenes via Copper-Catalyzed Aminobenzannulation of (o-Alkynyl)arylketones with Amines

Co-reporter:Mingliang Zhang, Wenqing Ruan, Hui-Jun Zhang, Weiwei Li, and Ting-Bin Wen

The Journal of Organic Chemistry 2016 Volume 81(Issue 4) pp:1696-1703

Publication Date(Web):February 1, 2016

DOI:10.1021/acs.joc.5b02340

A copper-catalyzed aminobenzannulation of (o-alkynyl)arylketones with amines has been developed. This method features the use of a cheap copper catalyst, the facile annulation involving various amines, and the good functional group tolerance.

Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

Co-reporter:Hui-Jun Zhang, Weidong Lin, Zhengjian Wu, Wenqing Ruan and Ting-Bin Wen

Chemical Communications 2015 vol. 51(Issue 16) pp:3450-3453

Publication Date(Web):28 Jan 2015

DOI:10.1039/C4CC10017D

A silver nitrate-mediated, efficient phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides was developed. This process provides a convenient route for the synthesis of a variety of 2-diarylphosphoryl benzothiazoles and thiazoles which are promising precursors of a series of hemilabile P,N-ligands with small bite angles.

Correction: Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

Co-reporter:Hui-Jun Zhang, Weidong Lin, Zhengjian Wu, Wenqing Ruan and Ting-Bin Wen

Chemical Communications 2015 vol. 51(Issue 94) pp:16871-16871

Publication Date(Web):03 Nov 2015

DOI:10.1039/C5CC90492G

Correction for ‘Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides’ by Hui-Jun Zhang et al., Chem. Commun., 2015, 51, 3450–3453.

Construction of Isoquinolin-1(2H)-ones by Copper-Catalyzed Tandem Reactions of 2-(1-Alkynyl)benzaldimines with Water

Co-reporter:Mingliang Zhang;Wenqing Ruan ;Ting-Bin Wen

European Journal of Organic Chemistry 2015 Volume 2015( Issue 27) pp:5914-5918

Publication Date(Web):

DOI:10.1002/ejoc.201500908

Abstract

The Cu(OAc)₂-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl)benzaldimines to give the corresponding isoquinolinium intermediates.

Palladium-Catalyzed Direct C2- and Further C7-Acylation of Indoles with Aldehydes

Co-reporter:Hui-Jun Zhang;Zhengjian Wu;Weidong Lin ;Ting-Bin Wen

Chinese Journal of Chemistry 2015 Volume 33( Issue 5) pp:517-521

Publication Date(Web):

DOI:10.1002/cjoc.201500059

Abstract

The palladium-catalyzed direct C2- and further C7-acylation of indoles with aldehydes have been developed. This method provides a convenient pathway toward a variety of mono- and diacylated indoles.

Copper-Catalyzed Direct C2-Benzylation of Indoles with Alkylarenes

Co-reporter:Hui-Jun Zhang, Feng Su, and Ting-Bin Wen

The Journal of Organic Chemistry 2015 Volume 80(Issue 22) pp:11322-11329

Publication Date(Web):November 11, 2015

DOI:10.1021/acs.joc.5b01935

The copper-catalyzed regioselective cross-dehydrogenative coupling of N-pyrimidylindoles with benzylic C(sp3)–H bonds has been developed. Di-tert-butyl peroxide was employed as a mild oxidant, and benzaldehyde proved to be an effective additive. This reaction provides a direct and pratical route to a variety of 2-benzylindoles.

Rh(III)-Catalyzed Oxidative Coupling of Benzoic Acids with Geminal-Substituted Vinyl Acetates: Synthesis of 3-Substituted Isocoumarins

Co-reporter:Mingliang Zhang, Hui-Jun Zhang, Tiantian Han, Wenqing Ruan, and Ting-Bin Wen

The Journal of Organic Chemistry 2015 Volume 80(Issue 1) pp:620-627

Publication Date(Web):December 1, 2014

DOI:10.1021/jo502231y

The Rh(III)-catalyzed C–H activation initiated cyclization of benzoic acids with electron-rich geminal-substituted vinyl acetates was described. The reaction was employed to prepare a range of 3-aryl and 3-alkyl substituted isocoumarins selectively.

Copper-catalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols

Co-reporter:Mingliang Zhang, Wen-Ting Lu, Wenqing Ruan, Hui-Jun Zhang, Ting-Bin Wen

Tetrahedron Letters 2014 Volume 55(Issue 10) pp:1806-1809

Publication Date(Web):5 March 2014

DOI:10.1016/j.tetlet.2014.01.120

An efficient and practical method for the construction of 2-aryl- and 2-alkyl-substituted benzothiazoles via a copper-catalyzed redox condensation process between benzothiazoles and aldehydes or benzylic alcohols has been developed. The reaction proceeded under mild reaction conditions using environmentally benign tert-butyl hydroperoxide (TBHP) as the oxidant. A reaction mechanism involving the ring-opening of benzothiazoles initiated by the attack of acyl radical on the thiazole ring and intramolecular condensation is proposed based on the isolation of an anilide disulfide intermediate.

Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

Co-reporter:Hui-Jun Zhang, Weidong Lin, Zhengjian Wu, Wenqing Ruan and Ting-Bin Wen

Chemical Communications 2015 - vol. 51(Issue 16) pp:NaN3453-3453

Publication Date(Web):2015/01/28

DOI:10.1039/C4CC10017D

Correction: Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

Co-reporter:Hui-Jun Zhang, Weidong Lin, Zhengjian Wu, Wenqing Ruan and Ting-Bin Wen

Chemical Communications 2015 - vol. 51(Issue 94) pp:NaN16871-16871

Publication Date(Web):2015/11/03

DOI:10.1039/C5CC90492G

Correction for ‘Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides’ by Hui-Jun Zhang et al., Chem. Commun., 2015, 51, 3450–3453.