Synthesis and properties of 2,3-dialkynyl-1,4-benzoquinones

被引：33

作者：

Hammershoj, Peter ^{[1
]}

Reenberg, Theis K. ^{[1
]}

Pittelkow, Michael ^{[1
]}

Nielsen, Christian B. ^{[1
]}

Hammerich, Ole ^{[1
]}

Christensen, Jorn B. ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen O, Denmark

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 12期

关键词：

benzoquinones; acetylenes; sonogashira cross-coupling; cyclic voltammetry; UV/Vis; DFT calculations;

D O I：

10.1002/ejoc.200600081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkynyl substituents can be used to tune the acceptor properties of benzoquinones due to their slight electron-withdrawing abilities. Applications of new acceptors rely on efficient and practical synthetic procedures. Herein we describe a general and convenient approach for the synthesis of 2,3-dialkynyl-1,4-benzoquinones using a combination of regiospecific aromatic substitution, Sonogashira cross-couplings and mild CAN oxidation chemistry. The regiochemical outcome of the synthetic protocol was verified by X-ray crystallography of two compounds. Cyclic voltammetry, UV/Vis and DFT calculations on three derivatives show that the symmetrical dialkynyl-substituted benzoquinones are attractive acceptors. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

引用

页码：2786 / 2794

页数：9

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