Synthesis of Azaheterocycles from Aryl Ketone O-Acetyl Oximes and Internal Alkynes by Cu-Rh Bimetallic Relay Catalysts

被引：219

作者：

Too, Pei Chui ^{[1
]}

Chua, Sze Hui ^{[1
]}

Wong, Siong Heng ^{[1
]}

Chiba, Shunsuke ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 15期

关键词：

H BOND FUNCTIONALIZATION; ONE-POT SYNTHESIS; AROMATIC IMINES; OXIDATIVE COUPLING/CYCLIZATION; CARBON-HYDROGEN; ACTIVATION; ANNULATION; DERIVATIVES; ALKYLATION; ARYLATION;

D O I：

10.1021/jo200897q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc)(2)-[Cp*RhCl2](2) bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu Rh bimetallic system could be applied for the synthesis of isoquinolines as well as beta-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.

引用

页码：6159 / 6168

页数：10

共 79 条

[71] Annulation of aromatic Imines via directed C-H bond activation [J].

Thalji, RK ;

Ahrendt, KA ;

Bergman, RG ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6775-6781

[72] Annulation of aromatic imines via directed C-H activation with Wilkinson's catalyst [J].

Thalji, RK ;

Ahrendt, KA ;

Bergman, RG ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9692-9693

[73] Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes [J].

Too, Pei Chui ;

Wang, Yi-Feng ;

Chiba, Shunsuke .

ORGANIC LETTERS, 2010, 12 (24) :5688-5691

[74] Rhodium-catalyzed arylation using arylboron compounds: Efficient coupling with aryl halides and unexpected multiple arylation of benzonitrile [J].

Ueura, K ;

Satoh, T ;

Miura, M .

ORGANIC LETTERS, 2005, 7 (11) :2229-2231

[75] Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C-H and C-C Bond Activation [J].

Wang, Congyang ;

Rakshit, Souvik ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14006-14008

[76] Intermolecular dienyl Pauson-Khand reaction [J].

Wender, PA ;

Deschamps, NM ;

Williams, TT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (23) :3076-3079

[77] Iron-Catalyzed Chemoselective ortho Arylation of Aryl Imines by Directed C-H Bond Activation [J].

Yoshikai, Naohiko ;

Matsumoto, Arimasa ;

Norinder, Jakob ;

Nakamura, Eiichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2925-2928

[78] The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization [J].

Yotphan, Sirilata ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2452-2453

[79] Synthesis of Isoquinolines via Rhodium(III)-Catalyzed Dehydrative C-C and C-N Coupling between Oximines and Alkynes [J].

Zhang, Xingping ;

Chen, Dan ;

Zhao, Miao ;

Zhao, Jing ;

Jia, Aiqun ;

Li, Xingwei .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (05) :719-723

← 1 2 3 4 5 6 7 8 →