Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process

被引：56

作者：

Bonin, Helene ^{[1
]}

Delbrayelle, Dominique ^{[2
]}

Demonchaux, Patrice ^{[2
]}

Gras, Emmanuel ^{[1
,3
,4
]}

机构：

[1] Univ Toulouse 3, CNRS, LSPCMIB, F-31062 Toulouse 9, France

[2] Minakem, F-59310 Beuvry La Foret, France

[3] CNRS, LCC, F-31077 Toulouse, France

[4] Univ Toulouse, INPT, UPS, LCC, F-31077 Toulouse, France

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 15期

关键词：

C-H BONDS; ARENEDIAZONIUM SALTS; ARYLBORONIC ACIDS; HYDROXYPHENYLBORONIC ACIDS; PALLADIUM; BORYLATION; COMPLEXES; CATALYSTS; WATER; CONVENIENT;

D O I：

10.1039/b926547n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Boronic esters have long been considered as poor partners in cross-coupling reactions with arene diazoniums. Here is reported an unprecedented application of self-activated boronic esters in a base-free cross-coupling reaction with diazonium salts under mild and user friendly conditions.

引用

页码：2677 / 2679

页数：3

共 39 条

[1] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS [J].

BELLER, M ;

FISCHER, H ;

HERRMANN, WA ;

OFELE, K ;

BROSSMER, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1848-1849

[2] A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles [J].

Billingsley, Kelvin L. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4695-4698

[3] 1-Phosphabarrelene complexes of palladium and their use in Suzuki-Miyaura coupling reactions [J].

Blug, Matthias ;

Guibert, Clement ;

Le Goff, Xavier-Frederic ;

Mezailles, Nicolas ;

Le Floch, Pascal .

CHEMICAL COMMUNICATIONS, 2009, (02) :201-203

[4] Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: A combined experimental and theoretical investigation [J].

Bottoni, A ;

Lombardo, M ;

Neri, A ;

Trombini, C .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3397-3405

[5] A DFT study of the full catalytic cycle of the Suzuki-Miyaura cross-coupling on a model system [J].

Braga, Ataualpa A. C. ;

Ujaque, Gregori ;

Maseras, Feliu .

ORGANOMETALLICS, 2006, 25 (15) :3647-3658

[6] Aryl trihydroxyborates: Easily isolated discrete species convenient for direct application in coupling reactions [J].

Cammidge, Andrew N. ;

Goddard, Victoria H. M. ;

Gopee, Hemant ;

Harrison, Nicola L. ;

Hughes, David L. ;

Schubert, Christopher J. ;

Sutton, Benjamin M. ;

Watts, Gary L. ;

Whitehead, Andrew J. .

ORGANIC LETTERS, 2006, 8 (18) :4071-4074

[7]

Chao JP, 2006, CHINESE J ORG CHEM, V26, P1004

[8] A fast synthetic route to GDP-sugars modified at the nucleobase [J].

Collier, Alice ;

Wagner, Gerd K. .

CHEMICAL COMMUNICATIONS, 2008, (02) :178-180

[9] A new approach to combretastatin D2 [J].

Cousin, D ;

Mann, J ;

Nieuwenhuyzen, M ;

van den Berg, H .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) :54-62

[10] Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium [J].

Darses, S ;

Jeffery, T ;

Genet, JP ;

Brayer, JL ;

Demoute, JP .

TETRAHEDRON LETTERS, 1996, 37 (22) :3857-3860

← 1 2 3 4 →