Original formation of benzyl benzoates by TDAE strategy

被引：11
作者：
Amiri-Attou, Ouassila [1 ]
Terme, Thierry [1 ]
Medebielle, Maurice [2 ]
Vanelle, Patrice [1 ]
机构：
[1] Univ Aix Marseille 2, Fac Pharm, CNRS, Lab Chim Organ Pharmaceut,UMR 6517, F-13385 Marseille 05, France
[2] Univ Lyon 1, CNRS INSA CPE, Lab Synth Electrosynth & React Composes Organ Flu, ICBMS,UMR 5246, F-69622 Villeurbanne, France
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 06期
关键词：
TDAE; aromatic aldehydes; benzyl benzoates; electron transfer;
D O I：
10.1016/j.tetlet.2007.12.011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report herein an original photoinduced electron transfer reaction between an aromatic aldehyde and TDAE in the presence of chloromethyl-dimethoxybenzenes. Thus, the reaction of 1-chloromethyl-2,5-dimethoxy-3,4,6-trimethylbenzene (1), dichlorides 4 and 5 with a series of aromatic aldehydes, in the presence of TDAE and under light catalysis, gave the corresponding benzyl benzoates. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1016 / 1020
页数：5
相关论文
共 39 条
[1]   Nucleophilic trifluoromethylation using trifluoromethyl iodide.: A new and simple alternative for the trifluoromethylation of aldehydes and ketones [J].
Aït-Mohand, S ;
Takechi, N ;
Médebielle, M ;
Dolbier, WR .
ORGANIC LETTERS, 2001, 3 (26) :4271-4273
[2]   Functionalization of 6-nitrobenzo[1,3]dioxole with carbonyl compounds via TDAE methodology [J].
Amiri-Attou, O ;
Terme, T ;
Vanelle, P .
MOLECULES, 2005, 10 (3-5) :545-551
[3]  
[Anonymous], ADV ELECT T
[4]  
ARCAMONE F, 1985, CANCER RES, V45, P5995
[5]   Convenient oxidation of alkylated phenols and methoxytoluenes to antifungal 1,4-benzoquinones with hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3) catalytic system in neutral ionic liquid [J].
Bernini, Roberta ;
Mincione, Enrico ;
Barontini, Maurizio ;
Fabrizi, Giancarlo ;
Pasqualetti, Marcella ;
Tempesta, Sabrina .
TETRAHEDRON, 2006, 62 (33) :7733-7737
[6]   New selective oxidation reactions by nitroarenes in basic medium involving electron-transfer processes [J].
Bjorsvik, HR ;
Liguori, L ;
Minisci, F .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (02) :136-140
[7]   Tetrakis(dimethylamino)ethylene as a useful reductant of some bromodifluoromethyl heterocycles.: Application to the synthesis of new gem-difluorinated heteroarylated compounds [J].
Burkholder, C ;
Dolbier, WR ;
Médebielle, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5385-5394
[8]  
COSSY J, 1996, ADV ELECT T, V5, P141
[9]   Generation of ketyl radical anions by photoinduced electron transfer (PET) between ketones and amines. Synthetic applications [J].
Cossy, Janine ;
Belotti, Damien .
TETRAHEDRON, 2006, 62 (27) :6459-6470
[10]   Single electron transfer approaches to the practical synthesis of aromatic and heterocyclic-CF2H derivatives [J].
Dolbier, WR ;
Médebielle, M ;
Ait-Mohand, S .
TETRAHEDRON LETTERS, 2001, 42 (29) :4811-4814
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