Pd(II)-catalyzed synthesis of indoles from α-aryloxime O-pentafluorobenzoates via intramolecular aromatic C-H amination

被引：20

作者：

Chiba, Shunsuke ^{[1
]}

Zhang, Line ^{[1
]}

Sanjaya, Stephen ^{[1
]}

Ang, Gim Yean ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2010年 / 66卷 / 30期

关键词：

Indoles; Oximes; C-H amination; Vinyl nitrene; Palladium catalysts; NONREARRANGED MONOTERPENOID UNIT; NEBER REARRANGEMENT; CATALYZED REACTIONS; INHIBITORS; CYCLIZATION; ALKALOIDS; ALKYNES; AMIDES; DECOMPOSITION; HETEROCYCLES;

D O I：

10.1016/j.tet.2010.05.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Aryl-alpha-aminocarbonyloxime O-pentafluorobenzoates are found to be promising precursors for synthesis of 2,3-disubstituted indole derivatives catalyzed by PdCl(2)(MeCN)(2) in the presence of MgO as a base. The reaction is supposed to proceed via intramolecular aromatic C-H amination of a vinyl nitrene-palladium intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5692 / 5700

页数：9

共 46 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus [J].

Ambrus, Joseph I. ;

Kelso, Michael J. ;

Bremner, John B. ;

Ball, Anthony R. ;

Casadei, Gabriele ;

Lewis, Kim .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) :4294-4297

[3] Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Aznar, Fernando ;

Valdes, Carlos .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :4031-4041

[4] Novel indole inhibitors of IMPDH from fragments: Synthesis and initial structure-activity relationships [J].

Beevers, RE ;

Buckley, GM ;

Davies, N ;

Fraser, JL ;

Galvin, FC ;

Hannah, DR ;

Haughan, AF ;

Jenkins, K ;

Mack, SR ;

Pitt, WR ;

Ratcliffe, AJ ;

Richard, MD ;

Sabin, V ;

Sharpe, A ;

Williams, SC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (09) :2539-2542

[5] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[6] Rh(II)-catalyzed isomerization of 2-Aryl-2H-azirines to 2,3-disubstituted indoles [J].

Chiba, Shunsuke ;

Hattori, Gaku ;

Narasaka, Koichi .

CHEMISTRY LETTERS, 2007, 36 (01) :52-53

[7]

CORNELIA H, 2000, EUR J ORG CHEM, V19, P3273

[8] Synthesis of indoles via domino reaction of N-aryl amides and ethyl diazoacetate [J].

Cui, Sun-Liang ;

Wang, Jing ;

Wang, Yan-Guang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13526-+

[9] Application of Ynamides in the Synthesis of 2-Amidoindoles [J].

Dooleweerdt, Karin ;

Ruhland, Thomas ;

Skrydstrup, Troels .

ORGANIC LETTERS, 2009, 11 (01) :221-224

[10] RHODIUM(II) ACETATE AND NAFION-H CATALYZED DECOMPOSITION OF N-ARYLDIAZOAMIDES - AN EFFICIENT SYNTHESIS OF 2(3H)-INDOLINONES [J].

DOYLE, MP ;

SHANKLIN, MS ;

PHO, HQ ;

MAHAPATRO, SN .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1017-1022

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