Co-reporter:Xin Yu, ZhenDong Huang, Wei Liu, SuPing Shi and ChunXiang Kuang
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 15) pp:4459-4465
Publication Date(Web):04 Mar 2015
DOI:10.1039/C5OB00102A
Palladium-catalyzed heteroarylation of 1-substituted 1,2,3-triazoles with furans and thiophenes has been developed in the presence of pyridine and Ag2CO3. The procedure is suitable for the regioselective preparation of 1,5-disubstituted 1,2,3-triazoles through conventional heating at reaction temperatures of 90–100 °C for 18 h.
Co-reporter:Ping He, Qingshan Tian and Chunxiang Kuang
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 26) pp:7146-7148
Publication Date(Web):28 May 2015
DOI:10.1039/C5OB00973A
A mild and efficient method for the direct alkenylation of 2-benzyl-1,2,3-triazoles via Pd-catalyzed C–H bond activation was developed. This protocol was compatible with various substrates and gave the corresponding products in good to excellent yields. Thus, the present study provides a novel and valuable method for the synthesis of 2-benzyl-1,2,3-triazole derivatives.
Co-reporter:Wei Liu, Xin Yu, Yahui Li and Chunxiang Kuang
Chemical Communications 2014 vol. 50(Issue 66) pp:9291-9294
Publication Date(Web):23 Jun 2014
DOI:10.1039/C4CC04129A
Using Ag2CO3 as an additive, we developed the Pd-catalyzed intermolecular C–H/C–H cross-coupling of pyridine N-oxides with five-membered heterocycles such as 1-benzyl-1,2,3-triazoles, thiophens and furans. This protocol provides an efficient and regioselective approach for the synthesis of unsymmetrical biheteroaryl molecules.
Co-reporter:Wei Liu, Xin Yu, and Chunxiang Kuang
Organic Letters 2014 Volume 16(Issue 6) pp:1798-1801
Publication Date(Web):March 12, 2014
DOI:10.1021/ol500542j
A highly efficient protocol for C2 selective alkenylation of electron-deficient thiazoles is developed. High C2 position selectivity for alkenylation products is achieved at a neutral environment, and a possible pathway of oxidative alkenylation is discussed. This methodology provides a simple way to construct a 2-alkenyl-thiazole moiety.
Co-reporter:Zechao Wang;Qinshan Tian;Xin Yu;Chunxiang Kuang
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 5) pp:961-966
Publication Date(Web):
DOI:10.1002/adsc.201300912
Co-reporter:Zechao Wang;Chunxiang Kuang
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 7) pp:1549-1554
Publication Date(Web):
DOI:10.1002/adsc.201400096
Co-reporter:Suping Shi, Wei Liu, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 22) pp:3576-3580
Publication Date(Web):04 Apr 2014
DOI:10.1039/C4OB00530A
A selective, efficient and catalytic ligand-free method for the direct arylation of 2-aryl-1,2,3-triazoles via Pd-catalyzed C–H bond activation is described. The process smoothly proceeds in moderate to excellent yields.
Co-reporter:Qingshan Tian, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 38) pp:7474-7477
Publication Date(Web):2014/08/13
DOI:10.1039/C4OB01406E
A palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes as an acyl source was developed. A wide variety of ketones containing 1,2,3-triazoles were obtained in good to excellent yields. This methodology provides a convenient access to the acylation of 2-substituted-1,2,3-triazoles.
Co-reporter:Qingshan Tian, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 33) pp:6349-6353
Publication Date(Web):08 Jul 2014
DOI:10.1039/C4OB01231C
A copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with sulfonylhydrazides through a tandem radical process was developed. This methodology provided an alternative strategy for the synthesis of sulfonated oxindoles by forming C–S, C–N and C–C bonds in a single operation.
Co-reporter:Yahui Li;Wei Liu;Qingshan Tian;Qing Yang;Chunxiang Kuang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 16) pp:3307-3312
Publication Date(Web):
DOI:10.1002/ejoc.201400126
Abstract
The palladium-catalyzed Suzuki cross-coupling of phenylhydrazine or (phenylsulfonyl)hydrazine was developed for the preparation of biaryl compound in high yields. Moreover, these hydrazines were also used in other cross-coupling reactions, and a possible pathway of this reaction was examined.
Co-reporter:Bo Xu;Wei Liu;Chunxiang Kuang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 12) pp:2576-2583
Publication Date(Web):
DOI:10.1002/ejoc.201400096
Abstract
A highly efficient protocol for regioselective synthesis of diaryl ketones by palladium-catalyzed direct acylation of arenes using thioethers as directing groups is reported. The possible pathway of direct acylation between thioethers and α-oxocarboxylic acids is discussed.
Co-reporter:Yiwen Yang;Chunxiang Kuang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 35) pp:7810-7813
Publication Date(Web):
DOI:10.1002/ejoc.201403211
Abstract
A new efficient method for the direct alkenylation of 3-arylsydnones by palladium-catalyzed C–H functionalization was developed. The reaction proceeded smoothly at room temperature and delivered the product in yields up to 83 %.
Co-reporter:Suping Shi and Chunxiang Kuang
The Journal of Organic Chemistry 2014 Volume 79(Issue 13) pp:6105-6112
Publication Date(Web):June 10, 2014
DOI:10.1021/jo5008306
Palladium-catalyzed alkoxylation of 2-aryl-1,2,3-triazoles was described in the presence of various groups in the aromatic rings. In addition, some other directing groups of heterocycles containing nitrogen were explored.
Co-reporter:Wei Liu, Yahui Li, Bo Xu, and Chunxiang Kuang
Organic Letters 2013 Volume 15(Issue 10) pp:2342-2345
Publication Date(Web):April 26, 2013
DOI:10.1021/ol401002w
Two highly efficient protocols for the regioselective synthesis of 2-substituted 4-alkenyl- and 4-aryl-1,2,3-triazoles by the palladium-catalyzed C–H functionalization of 1,2,3-triazole N-oxides are reported. A possible pathway of direct alkenylation with 1-octene and vinyl acetate is discussed.
Co-reporter:Wei Liu, Yahui Li, Yue Wang, and Chunxiang Kuang
Organic Letters 2013 Volume 15(Issue 18) pp:4682-4685
Publication Date(Web):September 10, 2013
DOI:10.1021/ol4019776
A highly efficient protocol for C–H/C–H cross-coupling has been found to occur between 2-aryl-1,2,3-triazole N-oxides and pyridine N-oxide derivatives. In addition, two homocoupling reactions of 2-substituted 1,2,3-triazole N-oxides and some pyridine N-oxide derivatives were developed. A possible pathway of C–H/C–H direct coupling is discussed.
Co-reporter:Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi and Chunxiang Kuang
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 45) pp:7830-7833
Publication Date(Web):03 Sep 2013
DOI:10.1039/C3OB41558A
A highly regioselective halogenation of 2-substituted-1,2,3-triazoles was developed via sp2 C–H activation. This method is compatible with halogen atoms, as well as electron-donating and electron-withdrawing groups. Meanwhile, the strategy is also efficient for the synthesis of a key intermediate of Suvorexant.
Co-reporter:Wei Liu;Yahui Li;Yue Wang;Chunxiang Kuang
European Journal of Organic Chemistry 2013 Volume 2013( Issue 24) pp:5272-5275
Publication Date(Web):
DOI:10.1002/ejoc.201300747
Abstract
An efficient route for the synthesis of 2,4-disubstituted 1,2,3-triazoles by the regioselective direct arylation of 2-aryl-1,2,3-triazole N-oxides with Ar–X [X = Br, I and B(OH)2] is demonstrated. The reaction proceeds through Pd-catalyzed C–H bond activation, and the influence of the aryl halides on the reactivity is investigated.
Co-reporter:Yiwen Yang;Hao Gong;Chunxiang Kuang
European Journal of Organic Chemistry 2013 Volume 2013( Issue 24) pp:5276-5281
Publication Date(Web):
DOI:10.1002/ejoc.201300765
Abstract
A mild and efficient method for the direct alkenylation of 5-pyrazoles by Pd-catalyzed C–H bond activation is described. The reaction smoothly proceeds at room temperature to provide products in up to 92 % yield.
Co-reporter:Zhongkui Zhang;Chunxiang Kuang
Chinese Journal of Chemistry 2013 Volume 31( Issue 8) pp:1011-1014
Publication Date(Web):
DOI:10.1002/cjoc.201300155
Abstract
1-Monosubstituted aliphatic 1,2,3-triazoles were synthesized by a one-pot reaction from aliphatic halides (Cl and Br), sodium azide and propiolic acid. The yields ranged from moderate to good. The reaction was easily carried out in DMF with Cs2CO3 at 100°C by copper-catalyzed click cycloaddition/decarboxylation.
Co-reporter:Xue-Zhi Cheng, Wei Liu, Zhen-Dong Huang, Chun-Xiang Kuang
Chinese Chemical Letters 2013 Volume 24(Issue 8) pp:764-766
Publication Date(Web):August 2013
DOI:10.1016/j.cclet.2013.05.007
A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields.A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields.
Co-reporter:Xiaokun Wang;Chunxiang Kuang;Qing Yang
European Journal of Organic Chemistry 2012 Volume 2012( Issue 2) pp:424-428
Publication Date(Web):
DOI:10.1002/ejoc.201101204
Abstract
A new methodology for the Cu-catalyzed synthesis of 1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide is presented. Aryl dibromoolefins were efficiently converted into the corresponding 1,2,3-triazoles. A comprehensive number of functional groups were compatible with this reaction. 1,2,3-Triazoles were obtained in moderate to excellent yields.
Co-reporter:Wensheng Zhang;Chunxiang Kuang;Qing Yang
Research on Chemical Intermediates 2012 Volume 38( Issue 1) pp:37-44
Publication Date(Web):2012 January
DOI:10.1007/s11164-011-0323-x
A series of phenyl azides bearing (E)-2-halovinyl groups were synthesized in high yields by treatment of (E)-3-(4-azidophenyl)- and (E)-3-(2-azidophenyl)acrylic acid with N-halosuccinimide in the presence of LiOAc. (E)-4-(2-bromovinyl) phenyl azide, one of the synthesized intermediates, was selected to transform to a diverse range of phenyl-1, 2, 3-triazoles bearing (E)-4-(2-bromovinyl) groups by Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction.
Co-reporter:Hui Jin ;Chunxiang Kuang
Chinese Journal of Chemistry 2011 Volume 29( Issue 3) pp:592-594
Publication Date(Web):
DOI:10.1002/cjoc.201190128
Abstract
Symmetrical diynes were synthesized by ligand-free copper-catalyzed homocoupling reaction of 1,1-dibromo-1-alkenes using a DBU/DMSO system at room temperature in good to excellent yields dot.−1.
Co-reporter:Ming Zhao, Chun Xiang Kuang, Xue Zhi Cheng, Qing Yang
Chinese Chemical Letters 2011 Volume 22(Issue 5) pp:571-574
Publication Date(Web):May 2011
DOI:10.1016/j.cclet.2010.11.022
A novel and convenient iron-catalyzed ketonization of 2-aryl-1,1-dibromoalkenes with KOAc has been achieved. A series of α-acetoxy aryl ketones were prepared with moderate yields via 2-carbon position functionalization of 2-aryl-1,1-dibromoalkenes.
Co-reporter:Hui Jin, Zhen Dong Huang, Chun Xiang Kuang, Xiao Kun Wang
Chinese Chemical Letters 2011 Volume 22(Issue 3) pp:310-313
Publication Date(Web):March 2011
DOI:10.1016/j.cclet.2010.10.024
An efficient and mild protocol for bromination of aryl azides with N-bromosuccinimide (NBS) under FeCl3 catalysis in 1,2-dichloroethane was developed. It is proved to be an efficient method for obtaining brominated aryl azides.
Co-reporter:Ming Zhao, Chunxiang Kuang, Qing Yang, Xuezhi Cheng
Tetrahedron Letters 2011 Volume 52(Issue 9) pp:992-994
Publication Date(Web):2 March 2011
DOI:10.1016/j.tetlet.2010.12.071
An unprecedented route to prepare terminal alkynes from 1,1-dibromo-1-alkenes mediated by Cs2CO3 was proven. 1,1-Dibromo-1-alkenes bearing various functional groups were efficiently converted to corresponding terminal alkynes in moderate to excellent yields.
Co-reporter:Xuezhi Cheng;Jun Jia;Chunxiang Kuang
Chinese Journal of Chemistry 2011 Volume 29( Issue 11) pp:2350-2354
Publication Date(Web):
DOI:10.1002/cjoc.201180402
Abstract
A convenient, efficient, and generally applicable method was developed for the synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids in the presence of DMSO and K2CO3.
Co-reporter:Yubo Jiang, Chunxiang Kuang, Qing Yang
Tetrahedron 2011 67(2) pp: 289-292
Publication Date(Web):
DOI:10.1016/j.tet.2010.11.051
Co-reporter:W. Zhang;C. Su;C. Kuang;Q. Yang
Russian Chemical Bulletin 2010 Volume 59( Issue 2) pp:452-456
Publication Date(Web):2010 February
DOI:10.1007/s11172-010-0100-9
Treatment of (E)-3-(4-azidophenyl)- and (E)-3-(2-azidophenyl)acrylic acid with N-halosuccinimides in the presence of LiOAc afforded high yields of phenylazides containing (E)-2-halovinyl group. The latter were transformed to different phenyl-1,2,3-triazoles bearing (E)-halovinyl group by the CuI-catalyzed reaction of 1,3-dipolar cycloaddition.
Co-reporter:Yu Bo Jiang, Chun Xiang Kuang
Chinese Chemical Letters 2009 Volume 20(Issue 5) pp:545-548
Publication Date(Web):May 2009
DOI:10.1016/j.cclet.2009.01.020
A convenient one-pot synthesis of functionalized (E)-2-arylvinyl bromides was achieved by microwave-induced deacetylation and subsequent acylation using dicyclohexyl carbodiimide (DCC) and dimethylamino-pyridine (DMAP) at room temperature from (E)-4-(2-bromovinyl)phenyl acetate.
Co-reporter:Wensheng Zhang;Chunxiang Kuang ;Qing Yang
Chinese Journal of Chemistry 2009 Volume 27( Issue 9) pp:1727-1732
Publication Date(Web):
DOI:10.1002/cjoc.200990291
Abstract
A novel method for the stereoselective synthesis of (Z)-4-(2-bromovinyl)benzenesulfonyl azide by simultaneous azidation and debrominative decarboxylation of anti-2,3-dibromo-3-(4-chlorosulfonylphenyl)propanoic acid using NaN3 only was developed. Facile transformation of (Z)-4-(2-bromovinyl)benzenesulfonyl azide to (Z)-N-[4- (2-bromovinyl)benzenesulfonyl]imidates was also achieved by Cu-catalyzed three-component coulping of (Z)-4-(2-bromovinyl)benzenesulfonyl azide, terminal alkynes and alcohols/phenols.
Co-reporter:Wensheng Zhang;Changhui Su;Yubo Jiang
Research on Chemical Intermediates 2009 Volume 35( Issue 5) pp:589-595
Publication Date(Web):2009 May
DOI:10.1007/s11164-009-0065-1
Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%.
Co-reporter:Yubo Jiang;Chunxiang Kuang
Journal of Chemical Sciences 2009 Volume 121( Issue 6) pp:
Publication Date(Web):2009 November
DOI:10.1007/s12039-009-0116-6
Highly functionalized (E)-2-arylvinyl bromides were prepared in high yields through a new convenient access by acylation of (E)-4-(2-bromovinyl)phenol with fatty and aromatic acids at room temperature using dicyclohexyl carbodiimide (DCC) and dimethylaminopyridine (DMAP).
Co-reporter:Qingshan Tian, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 38) pp:NaN7477-7477
Publication Date(Web):2014/08/13
DOI:10.1039/C4OB01406E
A palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes as an acyl source was developed. A wide variety of ketones containing 1,2,3-triazoles were obtained in good to excellent yields. This methodology provides a convenient access to the acylation of 2-substituted-1,2,3-triazoles.
Co-reporter:Yahui Li, Wei Liu and Chunxiang Kuang
Chemical Communications 2014 - vol. 50(Issue 54) pp:NaN7127-7127
Publication Date(Web):2014/05/12
DOI:10.1039/C4CC02546F
A method for achieving the direct arylation of pyridines with phenylhydrazine hydrochloride was developed in this study. This new reaction proceeds readily at room temperature without the use of any transition metal catalysts. This method allows rapid access to various arylated heterocycles that are more difficult to access through traditional methods.
Co-reporter:Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi and Chunxiang Kuang
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 45) pp:NaN7833-7833
Publication Date(Web):2013/09/03
DOI:10.1039/C3OB41558A
A highly regioselective halogenation of 2-substituted-1,2,3-triazoles was developed via sp2 C–H activation. This method is compatible with halogen atoms, as well as electron-donating and electron-withdrawing groups. Meanwhile, the strategy is also efficient for the synthesis of a key intermediate of Suvorexant.
Co-reporter:Xin Yu, ZhenDong Huang, Wei Liu, SuPing Shi and ChunXiang Kuang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 15) pp:NaN4465-4465
Publication Date(Web):2015/03/04
DOI:10.1039/C5OB00102A
Palladium-catalyzed heteroarylation of 1-substituted 1,2,3-triazoles with furans and thiophenes has been developed in the presence of pyridine and Ag2CO3. The procedure is suitable for the regioselective preparation of 1,5-disubstituted 1,2,3-triazoles through conventional heating at reaction temperatures of 90–100 °C for 18 h.
Co-reporter:Qingshan Tian, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 33) pp:NaN6353-6353
Publication Date(Web):2014/07/08
DOI:10.1039/C4OB01231C
A copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with sulfonylhydrazides through a tandem radical process was developed. This methodology provided an alternative strategy for the synthesis of sulfonated oxindoles by forming C–S, C–N and C–C bonds in a single operation.
Co-reporter:Wei Liu, Xin Yu, Yahui Li and Chunxiang Kuang
Chemical Communications 2014 - vol. 50(Issue 66) pp:NaN9294-9294
Publication Date(Web):2014/06/23
DOI:10.1039/C4CC04129A
Using Ag2CO3 as an additive, we developed the Pd-catalyzed intermolecular C–H/C–H cross-coupling of pyridine N-oxides with five-membered heterocycles such as 1-benzyl-1,2,3-triazoles, thiophens and furans. This protocol provides an efficient and regioselective approach for the synthesis of unsymmetrical biheteroaryl molecules.
Co-reporter:Ping He, Qingshan Tian and Chunxiang Kuang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 26) pp:NaN7148-7148
Publication Date(Web):2015/05/28
DOI:10.1039/C5OB00973A
A mild and efficient method for the direct alkenylation of 2-benzyl-1,2,3-triazoles via Pd-catalyzed C–H bond activation was developed. This protocol was compatible with various substrates and gave the corresponding products in good to excellent yields. Thus, the present study provides a novel and valuable method for the synthesis of 2-benzyl-1,2,3-triazole derivatives.
Co-reporter:Suping Shi, Wei Liu, Ping He and Chunxiang Kuang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 22) pp:NaN3580-3580
Publication Date(Web):2014/04/04
DOI:10.1039/C4OB00530A
A selective, efficient and catalytic ligand-free method for the direct arylation of 2-aryl-1,2,3-triazoles via Pd-catalyzed C–H bond activation is described. The process smoothly proceeds in moderate to excellent yields.