Zhenghu Xu

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Name: 徐政虎; ZhengHu Xu
Organization: Shandong University , China
Department: School of Chemistry and Chemical Engineering
Title: Associate Professor(PhD)

TOPICS

Co-reporter:Man Liang, Shuai Zhang, Jiong Jia, Chen-Ho Tung, Jianwu Wang, and Zhenghu Xu
Organic Letters May 19, 2017 Volume 19(Issue 10) pp:
Publication Date(Web):May 5, 2017
DOI:10.1021/acs.orglett.7b00804
An ultrafast synthesis of spiroketals by synergistic gold(I) and Sc(III) catalysis has been reported. Diverse 5,6-benzannulated spiroketals were rapidly constructed by the diastereoselective [4 + 2] cycloaddition between gold-generated enol ether and Sc(III)-catalyzed o-quinone methide intermediates. Ultrafast reaction rate, ambient reaction temperature, general scope, high yields, excellent diastereoselectivity, and good scalability are attractive features of this method.
Co-reporter:Shuyao Zhang, Beiming Cheng, Shen-An Wang, Ling Zhou, Chen-Ho Tung, Jianwu Wang, and Zhenghu Xu
Organic Letters 2017 Volume 19(Issue 5) pp:
Publication Date(Web):February 20, 2017
DOI:10.1021/acs.orglett.7b00090
An unprecedented gold-catalyzed cycloisomerization/1,5-H migration/Diels–Alder reaction cascade has been developed that enables the rapid construction of complex nitrogen polycyclic compounds. This one-pot, three-step cascade reaction offers good yields of the products and is promoted by a single gold catalyst under very mild conditions.
Co-reporter:Xianglong Peng, Chen Ma, Chen-Ho Tung, and Zhenghu Xu
Organic Letters 2016 Volume 18(Issue 17) pp:4154-4157
Publication Date(Web):August 23, 2016
DOI:10.1021/acs.orglett.6b02027
A copper-catalyzed three-component coupling reaction of in situ formed arynes, terminal alkynes, and benzenesulfonothioates is described. This reaction provides an efficient modular synthesis of o-alkynyl arylsulfides from easily available starting materials. This process involves one C–S bond and one C–C bond formation in one pot.
Co-reporter:Weiguo Wang, Fang Wei, Yudao Ma, Chen-Ho Tung, and Zhenghu Xu
Organic Letters 2016 Volume 18(Issue 17) pp:4158-4161
Publication Date(Web):August 23, 2016
DOI:10.1021/acs.orglett.6b02199
A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes to provide rapid access to 5-alkynyl-1,2,3-triazoles has been developed. The reaction proceeded via a copper-catalyzed alkyne azide cycloaddition followed by interception of the in situ formed cuprate–triazole intermediate with bromoalkyne. This reaction offers a new method to afford fully substituted triazoles in high yields with complete regioselectivity under mild reaction conditions.
Co-reporter:Bin Wang, Man Liang, Jian Tang, Yuting Deng, Jinhong Zhao, Hao Sun, Chen-Ho Tung, Jiong Jia, and Zhenghu Xu
Organic Letters 2016 Volume 18(Issue 18) pp:4614-4617
Publication Date(Web):August 30, 2016
DOI:10.1021/acs.orglett.6b02253
A novel early and late transition-metal relay catalysis has been developed by combining a gold-catalyzed cycloisomerization and a Yb(OTf)3-catalyzed diastereoselective [3 + 2] cycloaddition with aziridines in a selective C–C bond cleavage mode. Various biologically significant complex nitrogen-containing spiro heterocycles were rapidly constructed from readily available starting materials under mild conditions.
Co-reporter:Bin Wang, Ying Chen, Ling Zhou, Jianwu Wang and Zhenghu Xu  
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 3) pp:826-829
Publication Date(Web):17 Nov 2015
DOI:10.1039/C5OB02158H
A novel tandem metal relay catalytic system combining Zn(II)-catalyzed cycloisomerization and a Sc(III)-catalyzed carbonyl–ene reaction has been successfully developed. By using this unprecedented Zn/Sc bimetallic relay catalytic system, a variety of oxazole derivatives were obtained from easily available N-(propargyl)arylamides and aldehydes under mild conditions.
Co-reporter:Weiguo Wang;Xianglong Peng;Fang Wei; Chen-Ho Tung; Zhenghu Xu
Angewandte Chemie 2016 Volume 128( Issue 2) pp:659-663
Publication Date(Web):
DOI:10.1002/ange.201509124

Abstract

The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.

Co-reporter:Weiguo Wang;Xianglong Peng;Fang Wei; Chen-Ho Tung; Zhenghu Xu
Angewandte Chemie International Edition 2016 Volume 55( Issue 2) pp:649-653
Publication Date(Web):
DOI:10.1002/anie.201509124

Abstract

The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.

Co-reporter:Fang Wei, Haoyu Li, Chuanling Song, Yudao Ma, Ling Zhou, Chen-Ho Tung, and Zhenghu Xu
Organic Letters 2015 Volume 17(Issue 11) pp:2860-2863
Publication Date(Web):May 22, 2015
DOI:10.1021/acs.orglett.5b01342
A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.
Co-reporter:Weiguo Wang, Xianglong Peng, Xiaoyu Qin, Xiangyun Zhao, Chen Ma, Chen-Ho Tung, and Zhenghu Xu
The Journal of Organic Chemistry 2015 Volume 80(Issue 5) pp:2835-2841
Publication Date(Web):February 16, 2015
DOI:10.1021/jo5027673
An unprecedented palladium-catalyzed oxidative annulation of acrylamides with benzyne precursors has been successfully developed. By using this mild “N–H activation/Heck reaction” method, a wide variety of quinolinones were conveniently prepared in one step with high efficiency.
Co-reporter:Bin Wang, Ying Chen, Ling Zhou, Jianwu Wang, Chen-Ho Tung, and Zhenghu Xu
The Journal of Organic Chemistry 2015 Volume 80(Issue 24) pp:12718-12724
Publication Date(Web):November 30, 2015
DOI:10.1021/acs.joc.5b02382
A Zn(OTf)2-catalyzed tandem cycloisomerization/allylic alkylation of N-(propargyl)arylamides and allylic alcohols to produce oxazole derivatives has been successfully developed. The zinc catalyst served as π acid and also σ acid in this reaction. The target allylic oxazoles have been transformed into multisubstituted diene structures, which are potential aggregation-induced emission active optical materials.
Co-reporter:Fang Wei;Chuanling Song;Yudao Ma;Ling Zhou;Chen-Ho Tung
Science Bulletin 2015 Volume 60( Issue 17) pp:1479-1492
Publication Date(Web):2015 September
DOI:10.1007/s11434-015-0874-0
Diazo compounds are generally used as carbene precursors. Traditionally, dirhodium, copper and iron catalysts were used to decompose diazo compounds to form the key metal carbene intermediates. Recently, the gold catalysts have been developed as a unique type of metal catalyst to decompose diazo compounds. The derived gold carbene showed much different characters comparing with other transition metal carbenes. They could go through a series of cycloaddition, insertion and coupling reactions. Here, the recent progress of the gold carbene chemistry from diazo compounds was reviewed, including the scope of reactions, mechanism and synthetic applications.
Co-reporter:Shuo Zhang, Zhengliang Xu, Jiong Jia, Chen-Ho Tung and Zhenghu Xu  
Chemical Communications 2014 vol. 50(Issue 81) pp:12084-12087
Publication Date(Web):18 Aug 2014
DOI:10.1039/C4CC05610H
An efficient synthesis of spiroaminals over fused aminals has been successfully developed by bimetallic Au/Sc catalysis by using TMS as a traceless controlling group.
Co-reporter:Xianghua Wang, Shuli Dong, Zhili Yao, Lei Feng, Philias Daka, Hong Wang, and Zhenghu Xu
Organic Letters 2014 Volume 16(Issue 1) pp:22-25
Publication Date(Web):December 9, 2013
DOI:10.1021/ol4033286
A novel tandem metal relay catalytic system was developed by combining gold-catalyzed cycloisomerization with an early transition-metal-catalyzed inverse-electron-demand hetero-Diels–Alder (IED-HDA) reaction. Various biologically important spiroaminals and spiroketals were obtained with very high efficiency under mild conditions.
Co-reporter:Xianglong Peng, Weiguo Wang, Chao Jiang, Di Sun, Zhenghu Xu, and Chen-Ho Tung
Organic Letters 2014 Volume 16(Issue 20) pp:5354-5357
Publication Date(Web):October 2, 2014
DOI:10.1021/ol5025426
Strained alkynes include arynes and cyclooctynes reacted with N-methoxyamides through palladium-catalyzed C–H/N–H activation for the first time. A variety of important N-heterocycles such as phenanthridinones and isoquinolones were constructed in one step with high efficiency.
Co-reporter:Chuanling Song, Jianwu Wang and Zhenghu Xu  
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 31) pp:5802-5806
Publication Date(Web):09 Jun 2014
DOI:10.1039/C4OB00987H
Transmetalation is a key step in traditional coupling reactions. Herein we discuss the most recent progress in the metal–metal relay catalysis based on a transmetalation strategy. An efficient synthetic strategy for the formation of polysubstituted furan derivatives from cyclopropenes based on the tandem metal relay catalysis (TMRC reaction) is summarized.
Co-reporter:Shuo Zhang;Fang Wei;Chuangling Song;Jiong Jia
Chinese Journal of Chemistry 2014 Volume 32( Issue 10) pp:937-956
Publication Date(Web):
DOI:10.1002/cjoc.201400428

Abstract

Recently, homogeneous gold catalysis has attracted tremendous attention and has also been widely used in multistep synthesis. The current reaction methodology starts from the gold activation of unsaturated carbon bond and subsequent nucleophilic attack. The combination of a gold catalyst with another acid catalyst, including Bronsted acid and Lewis acid, is possible to bring two distinctive catalytic systems together and deliver unprecedented new reactions. More essentially, it avoids the purification of unstable intermediates and improves the step and atom economy. Here, the recent progress in the Au/Acid combined catalysis is reviewed, including the scope of reactions, mechanism and synthetic applications.

Co-reporter:Chuanling Song, Di Sun, Xianglong Peng, Jing Bai, Rongyi Zhang, Shengzhen Hou, Jianwu Wang and Zhenghu Xu  
Chemical Communications 2013 vol. 49(Issue 80) pp:9167-9169
Publication Date(Web):08 Aug 2013
DOI:10.1039/C3CC44762F
An efficient synthesis of bifurans via dimerization of cyclopropenes has been successfully developed using a copper-promoted cycloisomerization and palladium-catalyzed dimerization cascade. These novel bifuran structures possess interesting optoelectronic properties.
Co-reporter:Xianghua Wang, Zhili Yao, Shuli Dong, Fang Wei, Hong Wang, and Zhenghu Xu
Organic Letters 2013 Volume 15(Issue 9) pp:2234-2237
Publication Date(Web):April 19, 2013
DOI:10.1021/ol400803f
A novel sequential catalysis by combining gold catalysis with early transition metal catalysis was developed. Biologically important bicyclo[4.n.0] aminals were obtained under very mild conditions.
Co-reporter:Chuanling Song, Shuli Dong, Lei Feng, Xianglong Peng, Mingchao Wang, Jianwu Wang and Zhenghu Xu  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 37) pp:6258-6262
Publication Date(Web):01 Aug 2013
DOI:10.1039/C3OB41155A
A modular synthesis of tetrasubstituted furan carboxylates using a tandem cycloisomerization/oxidative carbonylation sequence of cyclopropenes has been successfully developed. The Tandem Metal Relay Catalysis (TMRC) pathway accounted for the high efficiency of this transformation.
Co-reporter:Chuanling Song;Lin Ju;Mingchao Wang;Pengcheng Liu;Yuanzhe Zhang; Jianwu Wang; Zhenghu Xu
Chemistry - A European Journal 2013 Volume 19( Issue 11) pp:3584-3589
Publication Date(Web):
DOI:10.1002/chem.201203997
Co-reporter:Lu Liu, Ryan Sarkisian, Zhenghu Xu, and Hong Wang
The Journal of Organic Chemistry 2012 Volume 77(Issue 17) pp:7693-7699
Publication Date(Web):August 10, 2012
DOI:10.1021/jo301070s
Novel enamine–metal Lewis acid bifunctional catalysts were successfully applied to the asymmetric Michael addition of ketones to alkylidene malonates, offering excellent stereoselectivity (up to >99% ee and >99:1 dr). The asymmetric Michael addition of ketones to allylidene malonates was also achieved.
Co-reporter:Shuyao Zhang, Chuan Shan, Shuai Zhang, Luye Yuan, Jianwu Wang, Chen-Ho Tung, Ling-Bao Xing and Zhenghu Xu
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 46) pp:NaN10980-10980
Publication Date(Web):2016/10/27
DOI:10.1039/C6OB02284G
A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed. A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(I) catalyst under mild conditions. The gold(I) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction. The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields.
Co-reporter:Chuanling Song, Yihua Sun, Jianwu Wang, Hui Chen, Jiannian Yao, Chen-Ho Tung and Zhenghu Xu
Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 10) pp:NaN1373-1373
Publication Date(Web):2015/08/06
DOI:10.1039/C5QO00205B
A new and efficient strategy for the synthesis of tetraaryl-substituted olefins has been developed. With a Cu/Pd-catalyzed isomerization/insertion/oxidative coupling cascade reaction of cyclopropene with internal alkynes, a wide variety of cis-tetrasubstituted olefins were synthesized in good yields as single stereoisomers. The photophysical properties of these novel tetraarylethenes were fully characterized and proved to be good AIE (aggregation-induced emission) luminogens. Experimental studies and theoretical calculation indicated that Cu(I) and Pd(II) were the actual catalysts. A novel deprotonative Cu-catalyzed cyclopropene cycloisomerization and subsequent successive Cu/Pd transmetalation relay mechanism was proposed for the discovered reaction.
Co-reporter:Shuo Zhang, Zhengliang Xu, Jiong Jia, Chen-Ho Tung and Zhenghu Xu
Chemical Communications 2014 - vol. 50(Issue 81) pp:NaN12087-12087
Publication Date(Web):2014/08/18
DOI:10.1039/C4CC05610H
An efficient synthesis of spiroaminals over fused aminals has been successfully developed by bimetallic Au/Sc catalysis by using TMS as a traceless controlling group.
Co-reporter:Chuanling Song, Di Sun, Xianglong Peng, Jing Bai, Rongyi Zhang, Shengzhen Hou, Jianwu Wang and Zhenghu Xu
Chemical Communications 2013 - vol. 49(Issue 80) pp:NaN9169-9169
Publication Date(Web):2013/08/08
DOI:10.1039/C3CC44762F
An efficient synthesis of bifurans via dimerization of cyclopropenes has been successfully developed using a copper-promoted cycloisomerization and palladium-catalyzed dimerization cascade. These novel bifuran structures possess interesting optoelectronic properties.
Co-reporter:Bin Wang, Ying Chen, Ling Zhou, Jianwu Wang and Zhenghu Xu
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 3) pp:NaN829-829
Publication Date(Web):2015/11/17
DOI:10.1039/C5OB02158H
A novel tandem metal relay catalytic system combining Zn(II)-catalyzed cycloisomerization and a Sc(III)-catalyzed carbonyl–ene reaction has been successfully developed. By using this unprecedented Zn/Sc bimetallic relay catalytic system, a variety of oxazole derivatives were obtained from easily available N-(propargyl)arylamides and aldehydes under mild conditions.
Co-reporter:Chuanling Song, Jianwu Wang and Zhenghu Xu
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 31) pp:NaN5806-5806
Publication Date(Web):2014/06/09
DOI:10.1039/C4OB00987H
Transmetalation is a key step in traditional coupling reactions. Herein we discuss the most recent progress in the metal–metal relay catalysis based on a transmetalation strategy. An efficient synthetic strategy for the formation of polysubstituted furan derivatives from cyclopropenes based on the tandem metal relay catalysis (TMRC reaction) is summarized.
Co-reporter:Chuanling Song, Shuli Dong, Lei Feng, Xianglong Peng, Mingchao Wang, Jianwu Wang and Zhenghu Xu
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 37) pp:NaN6262-6262
Publication Date(Web):2013/08/01
DOI:10.1039/C3OB41155A
A modular synthesis of tetrasubstituted furan carboxylates using a tandem cycloisomerization/oxidative carbonylation sequence of cyclopropenes has been successfully developed. The Tandem Metal Relay Catalysis (TMRC) pathway accounted for the high efficiency of this transformation.
Benzonitrile, 4-[5-[2-(4-methoxyphenyl)ethynyl]-1-(phenylmethyl)-1H-1,2,3-triazol-4-yl]-
1H-1,2,3-Triazol-5-amine, 1-[4-(1H-indol-1-yl)butyl]-4-phenyl-N,N-bis(phenylmethyl)-
1H-Isoindole-1,3(2H)-dione, 2-[4-[5-[bis(phenylmethyl)amino]-4-phenyl-1H-1,2,3-triazol-1-yl]butyl]-
1H-1,2,3-Triazol-5-amine, 1-(2-naphthalenylmethyl)-4-phenyl-N,N-bis(phenylmethyl)-
1H-1,2,3-Triazol-5-amine, 4-phenyl-N,N-bis(phenylmethyl)-1-(3-phenyl-2-propen-1-yl)-
1H-1,2,3-Triazol-5-amine, 1-[(4-nitrophenyl)methyl]-4-phenyl-N,N-bis(phenylmethyl)-
1H-1,2,3-Triazol-5-amine, 1-[(4-fluorophenyl)methyl]-4-phenyl-N,N-bis(phenylmethyl)-
1H-1,2,3-Triazol-5-amine, 1-[(4-methylphenyl)methyl]-4-phenyl-N,N-bis(phenylmethyl)-
1H-1,2,3-Triazol-5-amine, 4-(phenoxymethyl)-N,N,1-tris(phenylmethyl)-
1H-1,2,3-Triazol-5-amine, 4-butyl-N,N,1-tris(phenylmethyl)-