Palladium-Catalyzed Direct Benzylation of Azoles with Benzyl Carbonates

被引：123

作者：

Mukai, Tomoya ^{[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：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

关键词：

CROSS-COUPLING REACTIONS; SITE-SELECTIVE SP(2); DIRECT ARYLATION; C-H; DIHYDROFOLATE-REDUCTASE; AROMATASE INHIBITORS; BOND FORMATION; BREAST-CANCER; O-XYLYLENES; ARYL;

D O I：

10.1021/ol1002576

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct aromatic Sp(2) C-H benzylation of azole compounds with benzyl carbonates proceeds efficiently In the presence of a Pd-2(dba)(3)/dppp catalyst system and NaOAc as a base to afford the corresponding diarylmethanes in good yields. In addition, the same palladium catalyst enables the direct benzylic Sp(3) C-H benzylation with the second benzyl carbonates without employing any external base.

引用

页码：1360 / 1363

页数：4

共 75 条

[1] 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

[2] 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

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

Ackermann, Lutz ;

Novak, Petr .

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

[4] 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

[5] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[6] SAR study of a subtype selective allosteric potentiator of metabotropic glutamate 2 receptor, N-(4-phenoxyphenyl) N-(3-pyridinylmethyl)ethanesulfonamide [J].

Barda, DA ;

Wang, ZQ ;

Britton, TC ;

Henry, SS ;

Jagdmann, GE ;

Coleman, DS ;

Johnson, MP ;

Andis, SL ;

Schoepp, DD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (12) :3099-3102

[7] Iron-catalysed Negishi coupling of benzyl halides and phosphates [J].

Bedford, Robin B. ;

Huwe, Michael ;

Wilkinson, Mark C. .

CHEMICAL COMMUNICATIONS, 2009, (05) :600-602

[8] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 2005, 22 (02) :249-268

[9] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2007, 9 (26) :5397-5400

[10] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

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