Copper-mediated aerobic iodination and perfluoroalkylation of boronic acids with (CF3)2CFI at room temperature

作者: Xi-Hai Liu , Jing Leng , Su-Jiao Jia , Jian-Hong Hao , Fanglin Zhang

DOI: 10.1016/J.JFLUCHEM.2016.07.021

关键词:

摘要: Abstract The copper-mediated aerobic reactions between the branched (CF3)2CFI and boronic acids (R-B(OH)2) are described. Different from linear perfluoroalkyl analogs CF3(CF2)nI (n = 2, 3, 5, 7), reacting with R-B(OH)2 at room temperature under air in presence of catalytic Cu powder provided exclusively corresponding iodides (R-I), while arylboronic Cu(OAc)2 gave perfluoroalkylation products (R-CF(CF3)2) acceptable to moderate yields. iodination reaction could be further promoted by hydroquinone, addition which improved oxidation ability ipso-iodination high was facilitated copper carboxylates since these salts into mixtures successfully give rise Ar-CF(CF3)2.

参考文章(72)
David A. Nagib, Mark E. Scott, David W. C. MacMillan, Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis Journal of the American Chemical Society. ,vol. 131, pp. 10875- 10877 ,(2009) , 10.1021/JA9053338
Yuwen Zeng, Guangyu Li, Jinbo Hu, Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes Angewandte Chemie. ,vol. 54, pp. 10773- 10777 ,(2015) , 10.1002/ANIE.201503308
Dong-Fang Jiang, Chao Liu, Yong Guo, Ji-Chang Xiao, Qing-Yun Chen, A General, Regiospecific Synthetic Route to Perfluoroalkylated Arenes via Arenediazonium Salts with RFCu(CH3CN) Complexes European Journal of Organic Chemistry. ,vol. 2014, pp. 6303- 6309 ,(2014) , 10.1002/EJOC.201402820
Hiroshi Naka, Masanobu Uchiyama, Yotaro Matsumoto, Andrew E. H. Wheatley, Mary McPartlin, James V. Morey, Yoshinori Kondo, An Aluminum Ate Base: Its Design, Structure, Function, and Reaction Mechanism Journal of the American Chemical Society. ,vol. 129, pp. 1921- 1930 ,(2007) , 10.1021/JA064601N
Tomoko Yajima, Kanako Yamaguchi, Rie Hirokane, Emiko Nogami, Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides Journal of Fluorine Chemistry. ,vol. 150, pp. 1- 7 ,(2013) , 10.1016/J.JFLUCHEM.2013.02.019
Maurice Medebielle, Jean Pinson, Jean-Michel Savéant, Perfluoroalkylation of imidazoles by electrochemically induced srn1 substitution. Tetrahedron Letters. ,vol. 31, pp. 1279- 1282 ,(1990) , 10.1016/S0040-4039(00)88785-7
Eito Yoshioka, Shigeru Kohtani, Kaori Sawai, Kentefu, Eri Tanaka, Hideto Miyabe, Polarity-mismatched addition of electrophilic carbon radicals to an electron-deficient acceptor: cascade radical addition-cyclization-trapping reaction. Journal of Organic Chemistry. ,vol. 77, pp. 8588- 8604 ,(2012) , 10.1021/JO3015227
Maurice Médebielle, Mehmet Ali Oturan, Jean Pinson, Jean-Michel Savéant, A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced SRN1 Substitution Journal of Organic Chemistry. ,vol. 61, pp. 1331- 1340 ,(1996) , 10.1021/JO9515541
Bahiya Atouioual, Leonhard Hagmann, Pierre M.J. Jung, Emmanuel Lamy, Tammo Winkler, Atropisomerism about a heptafluoroisopropyl to aryl bond in 5-amino-4-heptafluoroisopropyl indazole Tetrahedron Letters. ,vol. 49, pp. 5403- 5404 ,(2008) , 10.1016/J.TETLET.2008.07.006