Cobalt-Catalyzed Cross-Coupling Between In Situ Prepared Arylzinc Halides and 2-Chloropyrimidine or 2-Chloropyrazine

被引：53

作者：

Begouin, Jeanne-Marie ^{[2
]}

Gosmini, Corinne ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Lab Heteroelements & Coordinat, F-91128 Palaiseau, France

[2] Univ Paris 12, CNRS, ICMPE, Inst Chim & Mat Paris Est,UMR 7182, F-94320 Thiais, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期

关键词：

O-IODOPHENYL KETONES; ALKYL-HALIDES; DIRECTED METALATION; DIAZINES PYRIDINES; AROMATIC KETONES; QUINOLINES; EFFICIENT; BROMIDES; ALKENYLATION; CARBOCYCLIZATION;

D O I：

10.1021/jo900240d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cobalt-catalyzed cross-coupling of aryl halides with 2-chloropyrimidines or 2-chloropyrazines is reported in satisfactory to high yields. The key step of this procedure is the formation of aromatic organozinc reagents and their coupling with 2-chlorodiazines using the same cobalt halide as catalyst and Zn dust under mild reaction conditions. This new cobalt-catalyzed coupling reaction represents a practical and interesting alternative to previously known methods for the synthesis of 2-aryldiazines.

引用

页码：3221 / 3224

页数：4

共 47 条

[1] Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the heck reaction [J].

Affo, Walter ;

Ohmiya, Hirohisa ;

Fujioka, Takuma ;

Ikeda, Yousuke ;

Nakamura, Tomoaki ;

Yorimitsu, Hideki ;

Oshima, Koichiro ;

Imamura, Yuki ;

Mizuta, Tsutomu ;

Miyoshi, Katsuhiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) :8068-8077

[2] First Cross-Coupling Reaction of Potassium Aryltrifluoroborates with Organic Chlorides in Aqueous Media Catalyzed by an Oxime-Derived Palladacycle [J].

Alacid, Emilio ;

Najera, Carmen .

ORGANIC LETTERS, 2008, 10 (21) :5011-5014

[3] Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate [J].

Amatore, Muriel ;

Gosmini, Corinne .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2089-2092

[4] Cobalt-catalyzed alkenylation of zinc organometallics [J].

Avedissian, H ;

Bérillon, L ;

Cahiez, G ;

Knochel, P .

TETRAHEDRON LETTERS, 1998, 39 (34) :6163-6166

[5]

BHATTI IA, 1997, J CHEM SOC P1, V24, P3581

[6] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[7] Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents [J].

Bonnet, V ;

Mongin, F ;

Trécourt, F ;

Quéguiner, G ;

Knochel, P .

TETRAHEDRON, 2002, 58 (22) :4429-4438

[8] Cobalt-catalyzed alkenylation of organomagnesium reagents [J].

Cahiez, G ;

Avedissian, H .

TETRAHEDRON LETTERS, 1998, 39 (34) :6159-6162

[9] Cobalt-catalyzed cross-coupling reaction between functionalized primary and secondary alkyl halides and aliphatic Grignard reagents [J].

Cahiez, Gerard ;

Chaboche, Christophe ;

Duplais, Christophe ;

Giulliani, Arianna ;

Moyeux, Alban .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) :1484-1488

[10] Microwave-assisted, efficient and regioselective Pd-catalyzed C-phenylation of halopyrimidines [J].

Ceide, Susana Conde ;

Montalban, Antonio Garrido .

TETRAHEDRON LETTERS, 2006, 47 (26) :4415-4418

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