Palladium- and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides

被引：83

作者：

Yao, Tomoyuki ^{[1
]}

Hirano, Koji ^{[1
]}

Satoh, Tetsuya ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 41期

关键词：

alkylation; azoles; C-H activation; nickel; palladium; C-H BOND; CROSS-COUPLING REACTIONS; GACL3-CATALYZED ORTHO-ETHYNYLATION; DIRECT ARYLATION; DIRECT ALKYNYLATION; CARBON-HYDROGEN; HIGHLY EFFICIENT; SUZUKI REACTIONS; ALKENYLATION; COPPER;

D O I：

10.1002/chem.201001631

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Long-ing alkyl chain: The catalytic direct C-H alkylation of azoles with unactivated alkyl bromides and chlorides is described. A palladium catalyst enables the alkylation of oxazoles, whereas a nickel one shows unique activity for thiazole. The catalyses allow a straightforward access to azole motifs bearing long, functional alkyl side chains. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12307 / 12311

页数：5

共 129 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].

Ackermann, Lutz ;

Barfuesser, Sebastian ;

Pospech, Jola .

ORGANIC LETTERS, 2010, 12 (04) :724-726

[3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[4] Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages [J].

Ackermann, Lutz ;

Novak, Petr .

ORGANIC LETTERS, 2009, 11 (21) :4966-4969

[5] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048

[6] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Fenner, Sabine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204

[7] 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

[8] 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

[9] GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines [J].

Amemiya, R ;

Fujii, A ;

Yamaguchi, M .

TETRAHEDRON LETTERS, 2004, 45 (22) :4333-4335

[10] Evidence for a NiI active species in the catalytic cross-coupling of alkyl electrophiles [J].

Anderson, TJ ;

Jones, GD ;

Vicic, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8100-8101

← 1 2 3 4 5 6 7 8 9 10 →