Denitrogenative Pd/Cu-catalyzed Suzuki-type Cross-coupling of Aryltrifluoroborates with Arylhydrazine Hydrochlorides in Water under Room Temperature

被引：13

作者：

Wang, Guofang ^{[1
]}

Meng, Mengting ^{[1
]}

Deng, Liping ^{[1
]}

Cheng, Kai ^{[1
,2
]}

Qi, Chenze ^{[1
]}

机构：

[1] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

[2] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2018年 / 32卷 / 03期

基金：

中国国家自然科学基金;

关键词：

arylhydrazide hydrochlorides; aryltrifluoroborates; Suzuki-type cross-coupling; water; water-soluble Pd-catalyzed; N BOND-CLEAVAGE; RADICAL ARYLATION; ORGANIC-SYNTHESIS; ARENEDIAZONIUM SALTS; TOSYL ARYLHYDRAZINES; TERMINAL ALKYNES; ARYL CHLORIDES; PALLADIUM; HYDRAZINES; ANILINES;

D O I：

10.1002/aoc.4203

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A water-soluble palladium-catalyzed Suzuki-type cross-coupling of aryltrifluoroborates with arylhydrazide hydrochlorides was efficiently developed under mild and environmentally benign conditions, in water without any ligand. The newly developed Pd/Cu co-catalyzed denitrogenative reaction gave a range of structurally diverse substituted biaryls with good to excellent yields, in which the byproduct was nitrogen.

引用

页数：9

共 75 条

[11] 2-N
[12] Copper-Catalyzed Coupling Reaction of Arylhydrazines and Trialkylphosphites
Chen, Sheng-Yan
Zeng, Run-Sheng
Zou, Jian-Ping
Asekun, Olayinka Taiwo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 1449 - 1453
[13] Palladium-Catalyzed Direct Denitrogenative C-3-Arylation of 1H-Indoles with Arylhydrazines using Air as the Oxidant
Chen, Yongxin
Guo, Shuaibo
Li, Kangning
Qu, Jinpeng
Yuan, Hua
Hua, Qiuru
Chen, Baohua
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) : 711 - 715
[14] Acid-promoted denitrogenative Pd-catalyzed addition of arylhydrazines with nitriles at room temperature
Cheng, Kai
Wang, Guofang
Meng, Mengting
Qi, Chenze
[J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (03): : 398 - 403
[15] Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water
Cheng, Kai
Zhao, Baoli
Hu, Sai
Zhang, Xian-Man
Qi, Chenze
[J]. TETRAHEDRON LETTERS, 2013, 54 (46) : 6211 - 6214
[16] Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions
Cheng, Kai
Wang, Chen
Ding, Yiyuan
Song, Qingbao
Qi, Chenze
Zhang, Xian-Man
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) : 9261 - 9268
[17] A General Palladium Catalyst System for Suzuki-Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates
Chow, Wing Kin
So, Chau Ming
Lau, Chak Po
Kwong, Fuk Yee
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) : 5109 - 5112
[18] Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids
Dai, Jian-Jun
Liu, Jing-Hui
Luo, Dong-Fen
Liu, Lei
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (02) : 677 - 679
[19] Potassium organotrifluoroborates: New perspectives in organic synthesis
Darses, Sylvain
Genet, Jean-Pierre
[J]. CHEMICAL REVIEWS, 2008, 108 (01) : 288 - 325
[20] desMeijere A., 2004, METAL CATALYZED CROS

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