Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes

被引：1

作者：

Yu, Xin ^{[1
]}

Huang, ZhenDong ^{[2
]}

Liu, Wei ^{[1
]}

Shi, SuPing ^{[1
]}

Kuang, ChunXiang ^{[1
,3
]}

机构：

[1] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China

[2] Zhejiang Citrus Res Inst, Taizhou 318020, Peoples R China

[3] Minist Educ, Key Lab Yangtze River Water Environm, Shanghai 200092, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ARYLATION SEQUENCE; BOND FORMATION; HECK REACTION; AZIDES; CYCLOADDITION; ALKYNES; METAL;

D O I：

10.1039/c5ob00102a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 degrees C for 18 h.

引用

页码：4459 / 4465

页数：7

共 53 条

[1] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles [J].

Ackermann, Lutz ;

Potukuchi, Harish K. ;

Landsberg, Dirk ;

Vicente, Ruben .

ORGANIC LETTERS, 2008, 10 (14) :3081-3084

[2] Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Born, Robert .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748

[3] Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates [J].

Ackermann, Lutz ;

Fenner, Sabine .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :430-432

[4] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus [J].

Ackermann, Lutz ;

Potukuchi, Harish Kumar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4503-4513

[5] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].

Ackermann, Lutz ;

Jeyachandran, Rajkumar ;

Potukuchi, Harish K. ;

Novak, Petr ;

Buettner, Lea .

ORGANIC LETTERS, 2010, 12 (09) :2056-2059

[6] Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air [J].

Ackermann, Lutz ;

Vicente, Ruben .

ORGANIC LETTERS, 2009, 11 (21) :4922-4925

[7] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[8] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[9] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[10] Palladium-catalyzed oxidative C-H/C-H cross-coupling of benzothiazoles with thiophenes and thiazoles [J].

Chen, Xuxing ;

Huang, Xiaojing ;

He, Qian ;

Xie, Yuyuan ;

Yang, Chunhao .

CHEMICAL COMMUNICATIONS, 2014, 50 (30) :3996-3999

← 1 2 3 4 5 6 →