Rhodium(III)-Catalyzed ortho-Arylation of Anilides with Aryl Halides

被引:41
作者
Haridharan, Radhakrishnan [1 ]
Muralirajan, Krishnamoorthy [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
C-C coupling; C-H activation; iodobenzene; N-phenylpivalamide; rhodium; homogeneous catalysis; C-H ACTIVATION; ONE-POT SYNTHESIS; CATALYZED ORTHO-ARYLATION; BOND ACTIVATION; N-METHOXYBENZAMIDES; INTERNAL ALKYNES; BORONIC ACIDS; COUPLING REACTIONS; EASY ROUTE; RHODIUM;
D O I
10.1002/adsc.201400798
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient o-arylation of pivalamides by aryl iodides via rhodium(III)-catalyzed C-H activation is demonstrated for the first time. Further, the biaryl products can be converted effectively into biologically active phenanthridine and phenanthridinone derivative.
引用
收藏
页码:366 / 370
页数:5
相关论文
共 84 条
[21]   Rhodium-Catalyzed Oxidative Annulation of Sulfoximines and Alkynes as an Approach to 1,2-Benzothiazines [J].
Dong, Wanrong ;
Wang, Long ;
Parthasarathy, Kanniyappan ;
Pan, Fangfang ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11573-11576
[22]   Allylic Carbon-Carbon Double Bond Directed Pd-Catalyzed Oxidative ortho-Olefination of Arenes [J].
Gandeepan, Parthasarathy ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :5738-5741
[23]   Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C-H Bond Activation and Enolate Cyclization [J].
Gandeepan, Parthasarathy ;
Parthasarathy, Kanniyappan ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) :8569-+
[24]   Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies [J].
Guimond, Nicolas ;
Gorelsky, Serge I. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) :6449-6457
[25]   The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles [J].
Huestis, Malcolm P. ;
Chan, Lina ;
Stuart, David R. ;
Fagnou, Keith .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) :1338-1341
[26]   Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cpt provide complementary selectivity [J].
Hyster, Todd K. ;
Rovis, Tomislav .
CHEMICAL COMMUNICATIONS, 2011, 47 (43) :11846-11848
[27]   Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation [J].
Hyster, Todd K. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10565-10569
[28]   4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors [J].
Ishida, J ;
Hattori, K ;
Yamamoto, H ;
Iwashita, A ;
Mihara, K ;
Matsuoka, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (19) :4221-4225
[29]   One-Pot Synthesis of Isoquinolinium Salts by Rhodium-Catalyzed C-H Bond Activation: Application to the Total Synthesis of Oxychelerythrine [J].
Jayakumar, Jayachandran ;
Parthasarathy, Kanniyappan ;
Cheng, Chien-Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :197-200
[30]   Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage [J].
Kakiuchi, Fumitoshi ;
Kochi, Takuya .
SYNTHESIS-STUTTGART, 2008, (19) :3013-3039