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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 2-3期

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

页码：366 / 370

页数：5

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

← 1 2 3 4 5 6 7 8 9 →