Palladium-Catalyzed Direct C-H Functionalization of Benzoquinone

被引：67

作者：

Walker, Sarah E. ^{[1
]}

Jordan-Hore, James A. ^{[1
]}

Johnson, David G. ^{[1
]}

Macgregor, Stuart A. ^{[1
]}

Lee, Ai-Lan ^{[1
]}

机构：

[1] Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 50期

基金：

英国工程与自然科学研究理事会;

关键词：

benzoquinone; CH functionalization; palladium; synthetic methods; water; ARYLBORONIC ACIDS; 1,4-BENZOQUINONE; ARYLQUINONES; ACTIVATION; ARYLATION; QUINONES;

D O I：

10.1002/anie.201408054

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct Pd-catalyzed CH functionalization of benzoquinone (BQ) can be controlled to give either mono- or disubstituted BQ, including the installation of two different groups in a one-pot procedure. BQ can now be directly functionalized with aryl, heteroaryl, cycloalkyl, and cycloalkene groups and, moreover, the reaction is conducted in environmentally benign water or acetone as solvents.

引用

页码：13876 / 13879

页数：4

共 37 条

[1] Recent Advances in 1,4-Benzoquinone Chemistry [J].

Abraham, Ignatious ;

Joshi, Rahul ;

Pardasani, Pushpa ;

Pardasani, R. T. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (03) :385-421

[2]

Batenko N. G., 2005, CHEM HETEROCYCL COMP, V41, P691

[3]

Bechtold T., 2009, HDB NATURAL COLORANT, DOI [10.1002/9780470744970, DOI 10.1002/9780470744970]

[4] Changing and challenging times for service crystallography [J].

Coles, Simon J. ;

Gale, Philip A. .

CHEMICAL SCIENCE, 2012, 3 (03) :683-689

[5] Perspectives on Medicinal Properties of Benzoquinone Compounds [J].

Dandawate, P. R. ;

Vyas, A. C. ;

Padhye, S. B. ;

Singh, M. W. ;

Baruah, J. B. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2010, 10 (05) :436-454

[6] Benzoquinone-Promoted Reaction of O2 with a PdII-Hydride [J].

Decharin, Nattawan ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5732-5735

[7] New and Efficient Protocol for Arylation of Quinones [J].

Demchuk, Oleg M. ;

Pietrusiewicz, K. Michal .

SYNLETT, 2009, (07) :1149-1153

[8] Palladium-catalyzed coupling of naphthoquinone triflates with stannanes. Unprecedented nucleophilic aromatic substitution on a hydroxynaphthoquinone triflate [J].

Echavarren, AM ;

deFrutos, O ;

Tamayo, N ;

Noheda, P ;

Calle, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4524-4527

[9] Practical C-H Functionalization of Quinones with Boronic Acids [J].

Fujiwara, Yuta ;

Domingo, Victoriano ;

Seiple, Ian B. ;

Gianatassio, Ryan ;

Del Bel, Matthew ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3292-3295

[10] An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-Step Synthesis of Leucomelone [J].

Gan, Xianwen ;

Jiang, Wei ;

Wang, Wei ;

Hu, Lihong .

ORGANIC LETTERS, 2009, 11 (03) :589-592

← 1 2 3 4 →