Palladium-Catalyzed C-H Bond Acylation of Acetanilides with Benzylic Alcohols under Aqueous Conditions

被引：36
作者：
Luo, Feihua [1 ,2 ]
Yang, Jun [1 ]
Li, Zhengkai [1 ]
Xiang, Haifeng [1 ]
Zhou, Xiangge [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Chengdu 610064, Peoples R China
[2] Sichuan Univ Arts & Sci, Dept Chem & Chem Engn, Dazhou 635000, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; Acylation; Radical reactions; C-H activation; Palladium; Reaction mechanisms; DECARBOXYLATIVE ORTHO-ACYLATION; SELECTIVE ARYLATION; OXIDATION LEVEL; N-ARYLATION; O BOND; ACTIVATION; PD; ARYL; EFFICIENT; ALDEHYDES;
D O I：
10.1002/ejoc.201500016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98%. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.
引用
收藏
页码：2463 / 2469
页数：7
相关论文
共 84 条
[1]   Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water [J].
Ackermann, Lutz ;
Pospech, Jola ;
Potukuchi, Harish Kumar .
ORGANIC LETTERS, 2012, 14 (08) :2146-2149
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]  
[Anonymous], 2010, Angew Chem Int Ed, DOI DOI 10.1002/ANGE.201002870
[4]   C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems [J].
Arockiam, Percia B. ;
Fischmeister, Cedric ;
Bruneau, Christian ;
Dixneuf, Pierre H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6629-6632
[5]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[6]   Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].
Basle, Olivier ;
Bidange, Johan ;
Shuai, Qi ;
Li, Chao-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149
[7]   Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant [J].
Chan, Chun-Wo ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :2999-3006
[8]  
Chen X., 2009, ANGEW CHEM, V121, P5196
[9]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[10]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086
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