Xin Lv

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Organization: Zhejiang Normal University

Department: Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Sciences

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TOPICS

Organic Chemistry

suzuki-miyaura Coupling

Chemicals
References

One-pot synthesis of thiazino[2,3,4-hi]indole derivatives through a tandem oxidative coupling/heteroannulation process

Co-reporter:Xi Mao;Tao Tong;Senbao Fan;Liting Fang;Jingyi Wu;Xiaoxia Wang;Honglan Kang

Chemical Communications 2017 vol. 53(Issue 34) pp:4718-4721

Publication Date(Web):2017/04/25

DOI:10.1039/C7CC00992E

A novel and expedient one-pot synthesis of thiazino[2,3,4-hi]indole derivatives from o-haloaryl enamines and o-bromothiophenols has been developed. The tandem oxidative coupling/heteroannulation reactions exhibit high selectivity and good efficiency. The polycyclic heterocyclic products obtained might be useful in medicinal chemistry and materials science.

Facile and Selective Synthesis of Imidazobenzimidazoles via a Copper-Catalysed Domino Addition/Cycloisomerisation/ Coupling Process

Co-reporter:Bingqing Xu;Bo Peng;Bili Cai;Shishi Wang;Xiaoxia Wang

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 4) pp:653-660

Publication Date(Web):

DOI:10.1002/adsc.201500455

Efficient domino synthesis of benzimidazole derivatives: copper catalysis versus transition metal-free conditions

Co-reporter:Haiquan Liu, Jiaming Tang, Liu Jiang, Tingting Zheng, Xiaoxia Wang, Xin Lv

Tetrahedron Letters 2015 Volume 56(Issue 13) pp:1624-1630

Publication Date(Web):25 March 2015

DOI:10.1016/j.tetlet.2015.01.197

An efficient and facile assembly of 2-substituted benzimidazoles and 2-benzimidazolones has been developed. Under very mild copper catalysis or transition metal-free conditions, a wide range of the 2-alkyl/alkenyl benzimidazole derivatives can be conveniently and selectively synthesized through the domino reactions of o-haloarylcarbodiimides with active methylene species. Interesting complimentary effect was discovered under the two different sets of conditions. Furthermore, a series of 1,3-disubstituted 2-benzimidazolones were facilely assembled from o-haloarylcarbodiimides and α,β-unsaturated esters.

Diastereoselective synthesis of cis-1,2-disubstituted cyclopropanols and cyclopent-3-enols via SmI2 mediated C–N(Bt) bond cleavage

Co-reporter:Tingting Xie, Liejin Zhou, Mengmeng Shen, Jianyong Li, Xin Lv, Xiaoxia Wang

Tetrahedron Letters 2015 Volume 56(Issue 26) pp:3982-3987

Publication Date(Web):24 June 2015

DOI:10.1016/j.tetlet.2015.05.002

Diastereoselective synthesis of cis-1,2-disubstituted cyclopropanols and cyclopent-3-enols has been achieved from readily available β-benzotriazolyl ketones (β-Bt ketones) via a C–N(Bt) bond cleavage/cyclization process promoted by SmI2/HMPA.

Allylsamarium Bromide-Mediated Cascade Cyclization of Homoallylic Esters. Synthesis of 2-(2-Hydroxyalkyl)cyclopropanols and 2-(2-Hydroxyethyl)bicyclo[2.1.1]hexan-1-ols

Co-reporter:Mengmeng Shen, Yawei Tu, Guanqun Xie, Qingsheng Niu, Hui Mao, Tingting Xie, Robert A. Flowers II, Xin Lv, and Xiaoxia Wang

The Journal of Organic Chemistry 2015 Volume 80(Issue 1) pp:52-61

Publication Date(Web):November 26, 2014

DOI:10.1021/jo501797w

In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive cascade cyclization of but-3-enyl but-3-enoates mediated by allylSmBr/HMPA/CuCl2·2H2O, in which the two C═C bonds were successively coupled to allow the construction of the structurally interesting bridged bicyclic tertiary alcohols. Thus, the 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols were prepared in moderate to good yields with excellent diastereoselectivity.

One-Pot Synthesis of Pyrrolo[3,2,1-kl]phenothiazines through Copper-Catalyzed Tandem Coupling/Double Cyclization Reaction

Co-reporter:Jiaming Tang, Bingqing Xu, Xi Mao, Hongyan Yang, Xiaoxia Wang, and Xin Lv

The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:11108-11114

Publication Date(Web):October 2, 2015

DOI:10.1021/acs.joc.5b01745

A novel and efficient synthesis of pyrrolo[3,2,1-kl]phenothiazines has been developed through a Cu(I)-catalyzed tandem C–S coupling/double cyclization process. Using 2-alkynyl-6-iodoanilines and o-bromobenzenethiols as the starting materials, a wide range of pyrrolo[3,2,1-kl]phenothiazine derivatives were facilely and efficiently generated in one pot under Cu(I) catalysis.

An efficient and facile synthesis of benzimidazo[1,2-a]benzimidazoles via copper-catalyzed domino addition/double cyclization

Co-reporter:Guodong Yuan, Haiquan Liu, Jilong Gao, Hongjuan Xu, Liu Jiang, Xiaoxia Wang and Xin Lv

RSC Advances 2014 vol. 4(Issue 42) pp:21904-21908

Publication Date(Web):07 May 2014

DOI:10.1039/C4RA01181C

A copper-catalyzed synthesis of benzimidazo[1,2-a]benzimidazoles by domino addition/double cyclization of bis-(o-haloaryl)carbodiimides with primary amines was developed. A variety of the desired polycyclic benzimidazoles were efficiently and facilely assembled. Multibonds and polycyclic moieties were directly constructed in one pot. 2-Bromo-2′-iodo-diarylcarbodiimides gave good selectivity.

Synthesis of benzimidazo[2,1-b]benzothiazole derivatives through sequential Cu-catalyzed domino coupling and Pd-catalyzed Suzuki reaction

Co-reporter:Jilong Gao, Jiaoyan Zhu, Lubin Chen, Yingying Shao, Jiaqi Zhu, Yijia Huang, Xiaoxia Wang, Xin Lv

Tetrahedron Letters 2014 Volume 55(Issue 22) pp:3367-3373

Publication Date(Web):28 May 2014

DOI:10.1016/j.tetlet.2014.04.070

A variety of benzo[d]benzo[4,5]imidazo[2,1-b]thiazoles were efficiently and conveniently synthesized from the Cu-catalyzed domino coupling of o-dihaloarenes with 2-mercaptobenzimidazoles. The reaction is also applicable to a series of multi-functional substrates, affording the halo-containing products with excellent selectivity. The brominated products can further react with arylboronic acids under Pd catalysis to furnish the aryl-substituted benzimidazo[2,1-b]benzothiazole derivatives.Graphical abstract

One-Pot Approach to 1,2-Disubstituted Indoles via Cu(II)-Catalyzed Coupling/Cyclization under Aerobic Conditions and Its Application for the Synthesis of Polycyclic Indoles

Co-reporter:Jilong Gao, Yingying Shao, Jiaoyan Zhu, Jiaqi Zhu, Hui Mao, Xiaoxia Wang, and Xin Lv

The Journal of Organic Chemistry 2014 Volume 79(Issue 19) pp:9000-9008

Publication Date(Web):September 11, 2014

DOI:10.1021/jo501250u

A straightforward assembly of 1,2-disubstituted indoles has been developed through a Cu(II)-catalyzed domino coupling/cyclization process. Under aerobic conditions, a wide range of 1,2-disubstituted indole derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under the Cu catalysis, afforded the indolo[1,2-f]phenanthridines via Pd-catalyzed intramolecular direct C(sp2)–H arylation. The one-pot tandem approaches to the polycyclic indole derivatives were also successfully achieved.

Copper-Catalyzed Domino Addition/Double Cyclization: An Approach to Polycyclic Benzimidazole Derivatives

Co-reporter:Guodong Yuan, Haiquan Liu, Jilong Gao, Kangjian Yang, Qingsheng Niu, Hui Mao, Xiaoxia Wang, and Xin Lv

The Journal of Organic Chemistry 2014 Volume 79(Issue 4) pp:1749-1757

Publication Date(Web):February 3, 2014

DOI:10.1021/jo402742k

An efficient and versatile method for the assembly of novel polycyclic benzimidazole derivatives has been developed by Cu-catalyzed domino addition/double cyclization reactions. A wide variety of polycyclic benzimidazole derivatives, which might be used as synthetic medicines and functional materials, were successfully assembled from bis-(o-haloaryl)carbodiimides. Unexpected N-methylated benzo[4,5]imidazo[1,2-a]indoles can also be selectively assembled. Multibonds and polycyclic moieties were conveniently formed in one pot during these domino processes.

Copper-Catalyzed Domino SN2/Coupling Reaction: A Versatile and Facile Synthesis of Cyclic Compounds from BaylisHillman Acetates

Co-reporter:Qingsheng Niu;Hui Mao;Guodong Yuan;Jilong Gao;Haiquan Liu;Yawei Tu;Xiaoxia Wang

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 6) pp:1185-1192

Publication Date(Web):

DOI:10.1002/adsc.201201033

Abstract

A variety of substituted quinoline/pyridine, thiochromene and naphthalene derivatives, which might be of biological and medicinal value, were synthesized by copper-catalyzed domino S_N2′/coupling, S_N2′/deacylation/coupling and S_N2′/coupling/elimination reactions. The method provides a general and convenient approach to the synthesis of various substituted cyclic compounds from the corresponding Baylis–Hillman (B-H) acetates and N-/S-/C-nucleophiles.

Reactivity of AllylSmBr/HMPA: Facile Synthesis of 3-Aryl-1,2,4-benzotriazines

Co-reporter:Ruifeng Yin;Liejin Zhou;Huili Liu;Hui Mao;Xin Lü;Xiaoxia Wang

Chinese Journal of Chemistry 2013 Volume 31( Issue 1) pp:143-148

Publication Date(Web):

DOI:10.1002/cjoc.201200989

Abstract

3-Aryl-1,2,4-benzotriazines were conveniently prepared in moderate to good yields from 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide/hexamethylphosphramide (allylSmBr/HMPA). Preliminary results indicate that HMPA may enhance the reducing ability as well as prohibit the nucleophicility of allylSmBr, thus making allylSmBr/HMPA as a promising single-electron transfer (SET) reagent.

Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

Co-reporter:Yawei Tu, Liejin Zhou, Ruifeng Yin, Xin Lv, Robert A. Flowers II, Kimberly A. Choquette, Huili Liu, Qingsheng Niu and Xiaoxia Wang

Chemical Communications 2012 vol. 48(Issue 89) pp:11026-11028

Publication Date(Web):19 Sep 2012

DOI:10.1039/C2CC34630C

The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization–ring-opening–anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl)cyclopropanols from readily available materials.

Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles

Co-reporter:Ziming Xia, Xin Lv, Wencun Wang, Xiaoxia Wang

Tetrahedron Letters 2011 Volume 52(Issue 38) pp:4906-4910

Publication Date(Web):21 September 2011

DOI:10.1016/j.tetlet.2011.07.057

Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles has been achieved by controlling the conditions. Thus, three types of products, namely α,β-unsaturated thioesters, β-thiophenoxy substituted N-acylbenzotriazoles, and β-thiophenoxy substituted thioesters were selectively obtained in good to excellent yields.

Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

Co-reporter:Yawei Tu, Liejin Zhou, Ruifeng Yin, Xin Lv, Robert A. Flowers II, Kimberly A. Choquette, Huili Liu, Qingsheng Niu and Xiaoxia Wang

Chemical Communications 2012 - vol. 48(Issue 89) pp:NaN11028-11028

Publication Date(Web):2012/09/19

DOI:10.1039/C2CC34630C

One-pot synthesis of thiazino[2,3,4-hi]indole derivatives through a tandem oxidative coupling/heteroannulation process

Co-reporter:Xi Mao, Tao Tong, Senbao Fan, Liting Fang, Jingyi Wu, Xiaoxia Wang, Honglan Kang and Xin Lv

Chemical Communications 2017 - vol. 53(Issue 34) pp:NaN4721-4721

Publication Date(Web):2017/04/04

DOI:10.1039/C7CC00992E