Benzannulation via Ruthenium-Catalyzed Diol-Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes

被引：46

作者：

Geary, Laina M. ^{[1
]}

Chen, Te-Yu ^{[1
]}

Montgomery, T. Patrick ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 16期

基金：

美国国家科学基金会;

关键词：

LARGER ACENES; DEOXYDEHYDRATION; HYDROXYCARBONYL; HETEROACENES; COMPLEXES; CHEMISTRY; FISSION;

D O I：

10.1021/ja502659t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.

引用

页码：5920 / 5922

页数：3

共 2 条

[1] Ruthenium-catalyzed formal [4+2] cycloaddition of alkynes with alkenes: formation of cyclohexenedicarboxylates via isomerization of alkynes and successive Diels-Alder reaction
Shiotsuki, M
Ura, Y
Ito, T
Wada, K
Kondo, T
Mitsudo, T
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (20) : 3168 - 3172
[2] Total Synthesis of the Phenylnaphthacenoid Type II Polyketide Antibiotic Formicamycin H via Regioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer [4+2] Cycloaddition
Hu, Guanyu
Doerksen, Rosalie S.
Ambler, Brett R.
Krische, Michael J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (38) : 26351 - 26359

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