Carbon radical addition–cyclization reaction induced by ruthenium-photocatalyst under visible light irradiation
作者： Eito Yoshioka , Shigeru Kohtani , Eri Tanaka , Yukari Hata , Hideto Miyabe
DOI: 10.1016/J.TET.2014.12.068
关键词: Ruthenium 、 Photocatalysis 、 Photochemistry 、 Catalysis 、 Carbon 、 Radical cyclization 、 Chemistry 、 Chlorine 、 Radical ion 、 Trifluoromethyl
摘要: In the presence of Ru(bpy)3Cl2·6H2O and (i-Pr)2NEt, photo-induced cascade radical addition–cyclization–trapping reaction proceeded in aqueous media. When i-C3F7I was employed as a precursor, iodine atom-transfer cyclization even absence (i-Pr)2NEt. Under conditions, ICH2CN ICH2CF3 also worked well carbon precursors. The reductive electron-transfer to CF3SO2Cl promoted chlorine cyclization.
elsevier.com
sci-hub.se 参考文章(125)
Dimitris Kalaitzakis, Tamsyn Montagnon, Ioanna Alexopoulou, Georgios Vassilikogiannakis, None, A Versatile Synthesis of Meyers’ Bicyclic Lactams from Furans: Singlet-Oxygen-Initiated Reaction Cascade Angewandte Chemie International Edition. ,vol. 51, pp. 8868- 8871 ,(2012) , 10.1002/ANIE.201204419
Davide Ravelli, Maurizio Fagnoni, Angelo Albini, Photoorganocatalysis. What for Chemical Society Reviews. ,vol. 42, pp. 97- 113 ,(2013) , 10.1039/C2CS35250H
Nobumasa Kamigata, Takeshi Ohtsuka, Takamasa Fukushima, Masato Yoshida, Toshio Shimizu, Direct perfluoroalkylation of aromatic and heteroaromatic compounds with perfluoroalkanesulfonyl chlorides catalysed by a ruthenium(II) phosphine complex Journal of the Chemical Society, Perkin Transactions 1. pp. 1339- 1346 ,(1994) , 10.1039/P19940001339
You-Quan Zou, Liang-Qiu Lu, Liang Fu, Ning-Jie Chang, Jian Rong, Jia-Rong Chen, Wen-Jing Xiao, Visible‐Light‐Induced Oxidation/[3+2] Cycloaddition/Oxidative Aromatization Sequence: A Photocatalytic Strategy To Construct Pyrrolo[2,1‐a]isoquinolines Angewandte Chemie. ,vol. 50, pp. 7171- 7175 ,(2011) , 10.1002/ANIE.201102306
Kazuki Miyazawa, Yusuke Yasu, Takashi Koike, Munetaka Akita, Visible-light-induced hydroalkoxymethylation of electron-deficient alkenes by photoredox catalysis Chemical Communications. ,vol. 49, pp. 7249- 7251 ,(2013) , 10.1039/C3CC42695E
Koichi Mikami, Yuichi Tomita, Yoshimitsu Itoh, Activation of CF Bonds in Preference to CI Bonds: Difluoromethylation of Lithium Enolates with Trifluoromethyl Iodide Angewandte Chemie. ,vol. 49, pp. 3819- 3822 ,(2010) , 10.1002/ANIE.201000435
Jean-Marc M. Grandjean, David A. Nicewicz, Synthesis of Highly Substituted Tetrahydrofurans by Catalytic Polar‐Radical‐Crossover Cycloadditions of Alkenes and Alkenols Angewandte Chemie. ,vol. 52, pp. 3967- 3971 ,(2013) , 10.1002/ANIE.201210111
Masafumi Ueda, Hideto Miyabe, Hisako Sugino, Takeaki Naito, Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids Organic and Biomolecular Chemistry. ,vol. 3, pp. 1124- 1128 ,(2005) , 10.1039/B418726A
Junlin Zhang, Leming Wang, Qi Liu, Zhen Yang, Yong Huang, Synthesis of α,β-unsaturated carbonyl compounds via a visible-light-promoted organocatalytic aerobic oxidation Chemical Communications. ,vol. 49, pp. 11662- 11664 ,(2013) , 10.1039/C3CC46778C
Durga Prasad Hari, Thea Hering, Burkhard König, The Photoredox‐Catalyzed Meerwein Addition Reaction: Intermolecular Amino‐Arylation of Alkenes Angewandte Chemie. ,vol. 53, pp. 725- 728 ,(2014) , 10.1002/ANIE.201307051