Palladium catalytic system for inhibition of O-arylation type reaction and regioselective direct arylation at C2 of phenols

被引：9

作者：

Beydoun, Kassem ^{[1
]}

Doucet, Henri ^{[1
]}

机构：

[1] Univ Rennes 1 Catalyse & Organometall, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2011年 / 1卷 / 07期

关键词：

ARYL BOND FORMATION; HALIDES; OXYGEN; FUNCTIONALIZATION; HETEROCYCLES; 4-ARYLATION; DERIVATIVES; BENZOFURANS; NAPHTHOLS; SOLVENTS;

D O I：

10.1039/c1cy00219h

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The palladium-catalysed arylation of free OH phenol derivatives proceeds regioselectively either at C2 or at OH with a variety of electron-deficient aryl bromides or heteroaryl bromides. The nature of the base was found to be crucial to control the regioselectivity of the reaction. In the presence of potassium acetate, the direct arylation at C2 is favoured; whereas, under the same reaction conditions, the use of potassium carbonate gave selectively the O-arylation type products.

引用

页码：1243 / 1249

页数：7

共 50 条

[41] Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C-H Activation Reaction
Hegde, Rajeev V.
Ong, Tiow-Gan
Ambre, Ram
Jadhav, Arvind H.
Patil, Siddappa A.
Dateer, Ramesh B.
CATALYSIS LETTERS, 2021, 151 (05) : 1397 - 1405
[42] Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates
Strotman, Neil A.
Chobanian, Harry R.
Guo, Yan
He, Jiafang
Wilson, Jonathan E.
ORGANIC LETTERS, 2010, 12 (16) : 3578 - 3581
[43] Regioselective C-2 or C-5 Direct Arylation of Pyrroles with Aryl Bromides using a Ligand-Free Palladium Catalyst
Roger, Julien
Doucet, Henri
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) : 1977 - 1990
[44] A Palladium/Copper Bimetallic Catalytic System: Dramatic Improvement for Suzuki-Miyaura-Type Direct C-H Arylation of Azoles with Arylboronic Acids
Liu, Bo
Qin, Xurong
Li, Kaizhi
Li, Xiyu
Guo, Qiang
Lan, Jingbo
You, Jingsong
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (39) : 11836 - 11839
[45] Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes
Liu, Can
Wang, Zhiming
Wang, Lei
Li, Pinhua
Zhang, Yicheng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (41) : 9209 - 9216
[46] Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N-Acyl Arylhydrazines
Cao, Jun
Chen, Zi-Li
Li, Shu-Min
Zhu, Gao-Feng
Yang, Yuan-Yong
Wang, Cong
Chen, Wen-Zhang
Wang, Jian-Ta
Zhang, Ji-Quan
Tang, Lei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) : 2774 - 2779
[47] Orientation effects on C2(5)-C2′(5′) linked bioxazole isomers synthesized via regioselective and sequential C-H arylation
Guo, Qiang
Tao, Li
Liu, Chuanqi
Zhao, Xiaoyun
Wan, Danyang
Zhang, Jincheng
Ai, Jianping
Li, Jie
CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 425 - 428
[48] (2-Pyridyl)acetone-Promoted Cu-Catalyzed O-Arylation of Phenols with Aryl Iodides, Bromides, and Chlorides
Zhang, Qi
Wang, Deping
Wang, Xianyang
Ding, Ke
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18): : 7187 - 7190
[49] Palladium-catalyzed regioselective direct C-H arylation of pyrazolo [3,4-d]pyrimidines
El Hafi, Mohamed
Naas, Mohammed
Loubidi, Mohammed
Jouha, Jabrane
Ramli, Youssef
Mague, Joel T.
Essassi, El Mokhtar
Guillaumet, Gerald
COMPTES RENDUS CHIMIE, 2017, 20 (9-10) : 927 - 933
[50] On-Water and Efficient Ullmann-Type O-Arylation Cross Coupling Reaction of Phenols and Aryl Tosylates in the Presence of Fe3O4@Starch-Au as Nanocatalyst
Mousavi-Mashhadi, Seyed Ali
Shiri, Ali
CHEMISTRYSELECT, 2021, 6 (16): : 3941 - 3951

← 1 2 3 4 5 →