Oxygenative Perfluoroalkylation of Olefinic Compounds Using Perfluoroalkyl Iodide in the Presence of Oxygen

Autor:	Masato Yoshida, Masahiko Iyoda, Tsunehiro Muraoka, Haruo Matsuyama, Masanori Ohkoshi
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Tris Trimethylsilyl Base (chemistry) Iodide chemistry.chemical_element Tributyltin hydride General Chemistry Silane Oxygen Medicinal chemistry Styrene chemistry.chemical_compound chemistry Organic chemistry
Zdroj:	Bulletin of the Chemical Society of Japan. 75:1833-1842
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.75.1833
Popis:	Reactions of perfluoroalkyl iodides with styrene and its derivatives were investigated under radical conditions in the presence of oxygen. The photochemical reaction of styrene with CF3(CF2)5I in the presence of tributyltin hydride or tris(trimethylsilyl)silane under an oxygen atmosphere afforded the corresponding perfluoroalkylated alcohols in moderate yields together with CF3(CF2)5H. However, the photochemical reactions of styrene and its derivatives with CF3(CF2)nI (n = 3, 5) in the presence of hexabutylditin under oxygen produced the perfluoroalkylated alcohols in good yields. Furthermore, the reactions of styrenes with CF3(CF2)nI (n = 3, 5, 9) and Na2S2O4 in the presence of a base under air formed the same alcohols in good yields. The alcohols were found to provide a novel type of α-fluoroalkylated styrenes by acidic dehydration. Perfluoroalkylated α,β-unsaturated ketones were synthesized by oxygenative perfluoroalkylations of α-chlorostyrene and its derivatives using CF3(CF2)nI (n = 3, 5) under radi...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b8b25438c292308faa9b8d0d5c812ea2 https://doi.org/10.1246/bcsj.75.1833 Zobrazit plný text záznamu