Influence of Solvent, Electron Acceptors and Arenes on Photochemical Decarboxylation of Free Carboxylic Acids via Single Electron Transfer (SET)
作者： Yasuharu Yoshimi , Shota Hayashi , Keisuke Nishikawa , Yoshiki Haga , Kousuke Maeda
DOI: 10.3390/MOLECULES15042623
关键词:
摘要: Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene the presence various acceptors 1,2-, 1,3-, 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, 1,4-dicyanonaphthalene. The reaction influenced by arenes, acceptors, solvent. best result achieved photoreaction biphenyl 1,4-dicyanonaphthalene aqueous acetonitrile.
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sci-hub.se 参考文章(20)
Hans-Jürgen Schäfer, Recent contributions of kolbe electrolysis to organic synthesis Electrochemistry IV. ,vol. 152, pp. 91- 151 ,(1990) , 10.1007/BFB0034365
Steven L. Murov, Handbook of photochemistry ,(1973)
Derek H.R. Barton, Yolande Hervé, Pierre Potier, Josiane Thierry, Manipulation of the cabboxyl groups of α-amino-acids and peptides using radical chemistry based on esters of -hydroxy-2-thiopyridone Tetrahedron. ,vol. 44, pp. 5479- 5486 ,(1988) , 10.1016/S0040-4020(01)86053-1
Yoshiaki Kurauchi, Hideo Nobuhara, Kazuya Ohga, Electron-Transfer-Initiated Photoreactions of 1-Methyl-2-phenyl-1-pyrrolinium Perchlorate with α-Heteroatom-Substituted Alkanoate Anions Bulletin of the Chemical Society of Japan. ,vol. 59, pp. 897- 905 ,(1986) , 10.1246/BCSJ.59.897
Maki Ohashi, Keisuke Nakatani, Hajime Maeda, Kazuhiko Mizuno, Photoinduced Tandem Three-Component Coupling of Propanedinitrile, 2,5-Dimethylhexa-2,4-diene, and Cyanoarenes Journal of Organic Chemistry. ,vol. 73, pp. 8348- 8351 ,(2008) , 10.1021/JO801624Q
Michael Oelgemöller, Axel G. Griesbeck, Photoinduced electron transfer chemistry of phthalimdes: an efficient tool for CC-bond formation Journal of Photochemistry and Photobiology C: Photochemistry Reviews. ,vol. 3, pp. 109- 127 ,(2002) , 10.1016/S1389-5567(02)00022-9
Kazuo Tsujimoto, Nobuhisa Nakao, Mamoru Ohashi, Electron-donating behaviour of aliphatic carboxylic acids in the photoreaction with 1,2,4,5-tetracyanobenzene Journal of The Chemical Society, Chemical Communications. pp. 366- 367 ,(1992) , 10.1039/C39920000366
Yasuharu Yoshimi, Miho Masuda, Tomoyuki Mizunashi, Keisuke Nishikawa, Kousuke Maeda, Nobumasa Koshida, Tatsuya Itou, Toshio Morita, Minoru Hatanaka, Inter- and Intramolecular Addition Reactions of Electron-Deficient Alkenes with Alkyl Radicals, Generated by SET-Photochemical Decarboxylation of Carboxylic Acids, Serve as a Mild and Efficient Method for the Preparation of γ-Amino Acids and Macrocyclic Lactones Organic Letters. ,vol. 11, pp. 4652- 4655 ,(2009) , 10.1021/OL9019277
David R. G. Brimage, R. Stephen Davidson, Peter R. Steiner, Use of heterocyclic compounds as photosensitisers for the decarboxylation of carboxylic acids Journal of the Chemical Society, Perkin Transactions 1. pp. 526- 529 ,(1973) , 10.1039/P19730000526
Tatsuya Itou, Yasuharu Yoshimi, Toshio Morita, Yuji Tokunaga, Minoru Hatanaka, Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions Tetrahedron. ,vol. 65, pp. 263- 269 ,(2009) , 10.1016/J.TET.2008.10.054