Metal-free synthesis of sterically crowded biphenyls by direct ar-h substitution in alkyl benzenes

被引：71

作者：

Dichiarante, Valentina ^{[1
]}

Tagnoni, Maurizio ^{[1
]}

Albini, Angelo ^{[1
]}

机构：

[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 34期

关键词：

aryl cations; arylation; cross-coupling; methylbenzenes; photochemistry;

D O I：

10.1002/anie.200701462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Four's definitely a crowd: The chemoselective activation of Ar-H bonds in methylbenzenes by treatment with photogenerated phenyl cations allowed the synthesis of sterically crowded biphenyl compounds, including tetra-ortho-substituted biphenyls, by intermolecular cross-coupling (see scheme). This method is an appealing metal-free alternative to widely used transition-metal catalysis. TFE = 2,2,2-trifluoroethanol. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6495 / 6498

页数：4

共 26 条

[1] 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

[2] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[3]

[Anonymous], ANGEW CHEM

[4] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[5] Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoheterolysis of aryl-oxygen bonds [J].

De Carolis, M ;

Protti, S ;

Fagnoni, M ;

Albini, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (08) :1232-1236

[6] A meta effect in organic photochemistry?: The case of SN1 reactions in methoxyphenyl derivatives [J].

Dichiarante, Valentina ;

Dondi, Daniele ;

Protti, Stefano ;

Fagnoni, Maurizio ;

Albini, Angelo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5605-5611

[7] A nanosecond laser flash photolysis study of aqueous 4-chlorophenol [J].

Durand, AP ;

Brown, RG ;

Worrall, D ;

Wilkinson, F .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 96 (1-3) :35-43

[8] First intermolecular palladium catalyzed arylation of an unfunctionalized aromatic hydrocarbon [J].

Dyker, G ;

Borowski, S ;

Heiermann, J ;

Körning, J ;

Opwis, K ;

Henkel, G ;

Köckerling, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 606 (02) :108-111

[9] Arylation reactions:: The photo-SN1 path via phenyl cation as an alternative to metal catalysis [J].

Fagnoni, M ;

Albini, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (09) :713-721

[10] Direct arylation of aromatic C-H bonds catalyzed by Cp*Ir complexes [J].

Fujita, K ;

Nonogawa, M ;

Yamaguchi, R .

CHEMICAL COMMUNICATIONS, 2004, (17) :1926-1927

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