Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions

被引：51

作者：

Itou, Tatsuya ^{[1
]}

Yoshimi, Yasuharu ^{[1
]}

Morita, Toshio ^{[1
]}

Tokunaga, Yuji ^{[2
]}

Hatanaka, Minoru ^{[1
]}

机构：

[1] Univ Fukui, Grad Sch Engn, Dept Appl Chem & Biotechnol, Fukui 9108507, Japan

[2] Univ Fukui, Grad Sch Engn, Dept Mat Sci & Engn, Fukui 9108507, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 01期

关键词：

PHOTOINDUCED ELECTRON-TRANSFER; REDOX-PHOTOSENSITIZED REACTIONS; AROMATIC-SUBSTITUTION REACTION; PHOTOCHEMICAL-REACTIONS; ARYL BROMIDES; CATALYZED CYANATION; PHYSICAL-PROPERTIES; OLEFIN COMBINATION; NEMATIC MIXTURES; HALIDES;

D O I：

10.1016/j.tet.2008.10.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photoreaction of dicyanobenzenes with aliphatic carboxylate ions afforded alkylcyanobenzenes and alkyldicyanobenzenes via decarboxylative Substitution. The redox-photosensitized reaction system was effective in improving the product yield. The efficiency of this photoreaction depended on the structure of the carboxylate ion, and the product distribution varied with the dicyanobenzenes employed. This photoreaction was proved to be a clean process for the preparation of alkylcyanobenzenes. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：263 / 269

页数：7

共 48 条

[1] ORIENTATIONAL ORDER IN THE NEMATOGENIC HOMOLOGOUS SERIES TRANS-4-ALKYL (4-CYANOPHENYL)-CYCLOHEXANE [J].

ABDOH, MMM ;

SRINIVASA ;

SHIVAPRAKASH, NC ;

PRASAD, JS .

JOURNAL OF CHEMICAL PHYSICS, 1982, 77 (05) :2570-2576

[2] Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates [J].

Anderson, BA ;

Bell, EC ;

Ginah, FO ;

Harn, NK ;

Pagh, LM ;

Wepsiec, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8224-8228

[3] THE PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION REACTION - METHANOL-ALPHA-PINENE-1,4-DICYANOBENZENE AND BETA-PINENE-1,4-DICYANOBENZENE - THE PHOTO-NOCAS REACTION [J].

ARNOLD, DR ;

DU, XY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7666-7667

[4] LUMINESCENCE QUENCHING OF STAR-(UO2F4)2- IN AQUEOUS-SOLUTION BY ANIONS [J].

BILLING, R ;

ZAKHAROVA, GV ;

ATABEKYAN, LS ;

HENNIG, H .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 59 (02) :163-174

[5] RADICAL IONS IN PHOTOCHEMISTRY .15. THE PHOTOSUBSTITUTION REACTION BETWEEN DICYANOBENZENES AND ALKYL OLEFINS [J].

BORG, RM ;

ARNOLD, DR ;

CAMERON, TS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (09) :1785-1802

[6] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

CHEMICAL REVIEWS, 1987, 87 (04) :779-794

[7] Palladium-catalyzed cross-coupling of B-benzyl-9-borabicyclo[3.3.1]nonane to furnish methylene-linked biaryls [J].

Flaherty, A ;

Trunkfield, A ;

Barton, W .

ORGANIC LETTERS, 2005, 7 (22) :4975-4978

[8] Electrochemical oxidation of tetrabutylammonium salts of aliphatic carboxylic acids in acetonitrile [J].

Galicia, M ;

González, FJ .

JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2002, 149 (03) :D46-D50

[9] Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air [J].

Grossman, O ;

Gelman, D .

ORGANIC LETTERS, 2006, 8 (06) :1189-1191

[10]

Grundmann C., 1985, METHODEN ORG CHEM E, VE5, P1313

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