Understanding the regioselectivity in Scholl reactions for the synthesis of oligoarenes

被引：43

作者：

Danz, Michael ^{[1
]}

Tonner, Ralf ^{[1
]}

Hilt, Gerhard ^{[1
]}

机构：

[1] Fachbereich Chem, D-35043 Marburg, Germany

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 03期

关键词：

DIELS-ALDER REACTIONS; OXIDANT; MECHANISM; EFFICIENT; DDQ;

D O I：

10.1039/c1cc15980a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short reaction sequence leads to oligoarene derivatives utilising a regioselective Scholl reaction for the unprecedented cyclisation to the mono-functionalised oligoarene under methanol elimination. Quantum-chemical investigations reveal the reason for the remarkably high regioselectivity.

引用

收藏

页码：377 / 379

页数：3

相关论文

共 29 条

[1] Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters [J].

Auvinet, Anne-Laure ;

Harrity, Joseph P. A. ;

Hilt, Gerhard .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) :3893-3896

[2] Stereoselective Formation of Triphenylene Ketals [J].

Boshta, Nader M. ;

Bomkamp, Martin ;

Schnakenburg, Gregor ;

Waldvogel, Siegfried R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3459-3466

[3] Synthesis of 2,2-functionalized benzo[1,3]dioxoles [J].

Boshta, Nader M. ;

Bomkamp, Martin ;

Waldvogel, Siegfried R. .

TETRAHEDRON, 2009, 65 (18) :3773-3779

[4] Regiodiverse Three-Component Synthesis of Arenes [J].

Danz, Michael ;

Hilt, Gerhard .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :303-308

[5] Graphene Nanoribbons by Chemists: Nanometer-Sized, Soluble, and Defect-Free [J].

Doessel, Lukas ;

Gherghel, Lileta ;

Feng, Xinliang ;

Muellen, Klaus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) :2540-2543

[6] Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Yamaoka, Nobutaka ;

Morimoto, Koji ;

Fujioka, Hiromichi ;

Kita, Yasuyuki .

TETRAHEDRON, 2009, 65 (52) :10797-10815

[7]

Donoghue PJ, 2006, CHEM-EUR J, V12, P7019

[8] A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions [J].

Goerigk, Lars ;

Grimme, Stefan .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (14) :6670-6688

[9] Ab initio studies of the radical cation Diels-Alder reaction [J].

Haberl, U ;

Wiest, O ;

Steckhan, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6730-6736

[10] KINETICS AND MECHANISMS OF REACTIONS OF ORGANIC CATION RADICALS IN SOLUTION [J].

HAMMERICH, O ;

PARKER, VD .

ADVANCES IN PHYSICAL ORGANIC CHEMISTRY, 1984, 20 :55-189