Palladium-Catalyzed Direct Synthesis of Carbazoles via One-Pot N-Arylation and Oxidative Biaryl Coupling: Synthesis and Mechanistic Study

被引：143

作者：

Watanabe, Toshiaki ^{[1
]}

Oishi, Shinya ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 13期

基金：

日本学术振兴会;

关键词：

C-H ACTIVATION; 1ST TOTAL-SYNTHESIS; PALLADIUM(0)-CATALYZED TANDEM CYCLIZATION; INTRAMOLECULAR DIRECT ARYLATION; PROTON-ABSTRACTION MECHANISM; CARBON BOND FORMATION; MOLECULAR-OXYGEN; AEROBIC OXIDATION; ARYL CHLORIDES; COORDINATED PALLADIUM(0);

D O I：

10.1021/jo9003376

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative Coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

引用

页码：4720 / 4726

页数：7

共 114 条

[1] Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives [J].

Abe, H ;

Nishioka, K ;

Takeda, S ;

Arai, M ;

Takeuchi, Y ;

Harayama, T .

TETRAHEDRON LETTERS, 2005, 46 (18) :3197-3200

[2] Arene C-H bond activation and arene oxidative coupling by cationic palladium(II) complexes [J].

Ackerman, LJ ;

Sadighi, JP ;

Kurtz, DM ;

Labinger, JA ;

Bercaw, JE .

ORGANOMETALLICS, 2003, 22 (19) :3884-3890

[3] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[4] CATALYTIC OXIDATIVE AROMATIC CYCLIZATIONS WITH PALLADIUM [J].

AKERMARK, B ;

OSLOB, JD ;

HEUSCHERT, U .

TETRAHEDRON LETTERS, 1995, 36 (08) :1325-1326

[5]

AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048

[6] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[7] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].

AMES, DE ;

OPALKO, A .

TETRAHEDRON, 1984, 40 (10) :1919-1925

[8] SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS [J].

AMES, DE ;

BULL, D .

TETRAHEDRON, 1982, 38 (03) :383-387

[9] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[10] A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation [J].

Bedford, RB ;

Cazin, CSJ .

CHEMICAL COMMUNICATIONS, 2002, (20) :2310-2311

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