Pd-catalyzed regioselective C-H chlorination of disubstituted 1,2,3-triazoles

被引：5

作者：

Ma, Xinyuan ^{[1
]}

Mo, Qiong ^{[1
]}

Chang, Jie ^{[1
]}

Xie, Kai ^{[1
]}

机构：

[1] Kunming Univ Sci & Technol, Fac Sci, Jingming South Rd 727, Kunming 650500, Yunnan, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2018年 / 48卷 / 12期

关键词：

1,2,3-Triazole; C-H activation; chlorination; Pd catalyst; DIRECT ARYLATIONS; COUPLING REACTIONS; ARYL CHLORIDES; METAL-FREE; PALLADIUM; CYCLOADDITION; CONSTRUCTION; HALOGENATION; NEGISHI; ACCESS;

D O I：

10.1080/00397911.2018.1455872

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper mainly studied Pd-catalyzed regioselective chlorination of disubstituted 1,2,3-triazoles directed by the 1,2,3-triazole ring. A series of regioselective chlorinated products were synthesized in 47-86% yields using Pd(OAc)(2) as a catalyst and CuCl2 as a chlorinated reagent. This method provides a new mean for the synthesis of 1,2,3-triazole halides which combines the formation of C-X bond with C-H activation. [GRAPHICS] .

引用

页码：1403 / 1412

页数：10

共 50 条

[31] Mechanistic Comparison between Pd-Catalyzed Ligand-Directed C-H Chlorination and C-H Acetoxylation
Stowers, Kara J.
Sanford, Melanie S.
ORGANIC LETTERS, 2009, 11 (20) : 4584 - 4587
[32] An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles
Ramachary, Dhevalapally B.
Krishna, Patoju M.
Gujral, Jagjeet
Reddy, G. Surendra
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16775 - 16780
[33] Copper(II)-promoted regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in water
Reddy, KR
Rajgopal, K
Kantam, ML
SYNLETT, 2006, (06) : 957 - 959
[34] A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry
Kumar, Dalip
Reddy, V. Buchi
Varma, Rajender S.
TETRAHEDRON LETTERS, 2009, 50 (18) : 2065 - 2068
[35] Harnessing the β-Silicon Effect for Regioselective and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization by Donor/Acceptor Carbenes Derived from 1-Sulfony1-1,2,3-triazoles
Garlets, Zachary J.
Davies, Huw M. L.
ORGANIC LETTERS, 2018, 20 (08) : 2168 - 2171
[36] Sulfonimidamide as a directing agent for Pd-catalyzed regioselective oxidative C-H acyloxylation of arenes
Jesin, C. P. Irfana
Ravindra, S.
Nandi, Ganesh Chandra
TETRAHEDRON, 2019, 75 (43)
[37] Pd-catalyzed, nondirected C-H aminations
Emmert, Marion H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[38] Base-Promoted Regiospecific Synthesis of Fully Substituted 1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazoles
Zhang, Xueying
Cui, Xue
Wang, Wei
Zeng, Tingting
Wang, Yan
Tan, Yinfeng
Liu, Dongyan
Wang, Xuesong
Li, Youbin
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2176 - 2183
[39] Ionic Liquid Catalyzed Efficient Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles Under Metal and Solvent Free Conditions
Banday, Abid H.
Hruby, Victor J.
CURRENT ORGANOCATALYSIS, 2021, 8 (02) : 223 - 227
[40] Palladium-catalyzed direct C-H ethoxycarbonylation of 2-aryl-1,2,3-triazoles and efficient synthesis of suvorexant
Sang, Rui
Zheng, Yang
Zhang, Hailong
Wu, Xiaohua
Wang, Qiantao
Hai, Li
Wu, Yong
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 648 - 652

← 1 2 3 4 5 →