Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones

被引:37
作者
Cao, Xiangxiang [1 ]
Bai, Yang [1 ]
Xie, Yanjun [1 ]
Deng, Guo-Jun [1 ,2 ]
机构
[1] Xiangtan Univ, Coll Chem, Minist Educ, Key Lab Environm Friendly Chem & Applicat, Xiangtan 411105, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100080, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
Aromatization; Arylation; Cyclohexanones; Dehydrogenation; Sulfonamides; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; N-ALKYLATION; AEROBIC OXIDATION; MOLECULAR-OXYGEN; AMINE FORMATION; C-N; RUTHENIUM; ALCOHOLS; NITROARENES;
D O I
10.1016/j.molcata.2013.11.023
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
Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of aryl sulfonamides with cyclohexanones. Various N-aryl sulfonamides were selectively obtained in good yields using molecular oxygen as oxidant. The reaction tolerated a wide range of functionalities. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:94 / 100
页数:7
相关论文
共 82 条
[21]   Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates [J].
Ge, Haibo ;
Niphakis, Micah J. ;
Georg, Gunda I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3708-+
[22]   Pd-Catalyzed Synthesis of Aryl Amines via Oxidative Aromatization of Cyclic Ketones and Amines with Molecular Oxygen [J].
Girard, Simon A. ;
Hu, Xiong ;
Knauber, Thomas ;
Zhou, Feng ;
Simon, Marc-Olivier ;
Deng, Guo-Jun ;
Li, Chao-Jun .
ORGANIC LETTERS, 2012, 14 (21) :5606-5609
[23]   Synthesis of Benzazepines by Gold-Catalysed Reactions of N-Allenylamides [J].
Gonzalez-Gomez, Alvaro ;
Dominguez, Gema ;
Perez-Castells, Javier .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (29) :5057-5062
[24]   TRANSITION METAL-CATALYZED N-ALKYLATION OF AMINES BY ALCOHOLS [J].
GRIGG, R ;
MITCHELL, TRB ;
SUTTHIVAIYAKIT, S ;
TONGPENYAI, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (12) :611-612
[25]   Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364
[26]   Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as Electrophiles [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
CHEMICAL REVIEWS, 2010, 110 (03) :1611-1641
[27]   Palladium-Catalyzed Aerobic Dehydrogenative Aromatization of Cyclohexanone Imines to Arylamines [J].
Hajra, Alakananda ;
Wei, Ye ;
Yoshikai, Naohiko .
ORGANIC LETTERS, 2012, 14 (21) :5488-5491
[28]   Borrowing hydrogen in the activation of alcohols [J].
Hamid, Malai Haniti S. A. ;
Slatford, Paul A. ;
Williams, Jonathan M. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1555-1575
[29]   Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860
[30]   Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides [J].
Hartwig, John F. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1534-1544