Catalytic photocarboxylation of 1,1-diphenylethylene with N,N,N',N'-tetramethylbenzidine and carbon dioxide

被引：16

作者：

Ito, Yoshikatsu ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 15期

关键词：

N; N'; N'-tetramethylbenzidine; carbon dioxide; catalytic photocarboxylation; high turnover number;

D O I：

10.1016/j.tet.2007.02.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photocarboxylation of 1,1 -diphenylethylene with N,N,N',N',-tetramethylbenzidine (TMB) in MeCN under bubbling Of CO2 proceeded with high catalytic efficiency, giving 3,3-diphenylacrylic acid (DPA) and 3-hydroxy-3,3-diphenylpropionic acid (20). The turnover number (TON=(DPA+20)/TMB) reached 17. Similarly, 1-phenyl-1-cyclohexene yielded cis-2-acetamido-2-phenylcyclohexanecarboxylic acid with TON 5.9. As compared with related N,N-dimethylaniline derivatives, TMB is more resistant to photodecomposition, has the much larger absorbance in the S-0 -> S-1 transition, and has the lower quenching efficiency by CO2. Probably these factors are partly responsible for the high TON observed for TMB. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3108 / 3114

页数：7

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