Intermolecular Decarboxylative Direct C-3 Arylation of Indoles with Benzoic Acids

被引：265

作者：

Cornella, Josep ^{[1
]}

Lu, Pengfei ^{[1
]}

Larrosa, Igor ^{[1
]}

机构：

[1] Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

INCLUDING FREE (NH)-IMIDAZOLE; H BOND FUNCTIONALIZATION; BIARYL SYNTHESIS; AROMATIC CARBOXYLATES; SELECTIVE ARYLATION; FREE (NH)-INDOLES; ROOM-TEMPERATURE; PALLADIUM; AZOLES; (NH)-BENZIMIDAZOLE;

D O I：

10.1021/ol902304n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium catalyzed C-H activation of indoles and a silver catalyzed decarboxylative C-C activation of ortho substituted benzoic acids are synergistically combined to synthesize indoles arylated exclusively in the C-3 position. This novel decarboxylative C-H arylation methodology is compatible with electron-donating and -withdrawing substituents in both coupling partners.

引用

页码：5506 / 5509

页数：4

共 54 条

[1] Palladium-Catalyzed Direct C-3 Arylations of Indoles with an Air-Stable HASPO [J].

Ackermann, Lutz ;

Barfuesser, Sebastian .

SYNLETT, 2009, (05) :808-812

[2]

AKITA Y, 1989, CHEM PHARM BULL, V37, P1477

[3] A warning on the use of radical traps as a test for radical mechanisms:: They react with palladium hydrido complexes [J].

Albéniz, AC ;

Espinet, P ;

López-Fernández, R ;

Sen, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11278-11279

[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]

[Anonymous], 2002, HDB ORGANOPALLADIUM

[6] Biaryl synthesis via decarboxylative Pd-catalyzed reactions of arenecarboxylic acids and diaryliodonium triflates [J].

Becht, Jean-Michel ;

Le Drian, Claude .

ORGANIC LETTERS, 2008, 10 (14) :3161-3164

[7] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].

Becht, Jean-Michel ;

Catala, Cedric ;

Le Drian, Claude ;

Wagner, Alain .

ORGANIC LETTERS, 2007, 9 (09) :1781-1783

[8] Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].

Bellina, F ;

Cauteruccio, S ;

Rossi, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382

[9] Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions [J].

Bellina, Fabio ;

Benelli, Francesca ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5529-5535

[10] Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides [J].

Bellina, Fabio ;

Calandri, Chiara ;

Cauteruccio, Silvia ;

Rossi, Renzo .

TETRAHEDRON, 2007, 63 (09) :1970-1980

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