首页 | 本学科首页   官方微博 | 高级检索  
     检索      


An efficient photoinduced iodoperfluoroalkylation of carbon-carbon unsaturated compounds with perfluoroalkyl iodides
Authors:Tsuchii Kaname  Imura Motohiro  Kamada Nagisa  Hirao Toshikazu  Ogawa Akiya
Institution:Department of Chemistry, Faculty of Science, Nara Women's University, Kitauoyanishi-machi, Nara 630-8506, Japan,.
Abstract:Dependent on the selection of the light sources employed, the photoinduced iodoperfluoroalkylation of a variety of unsaturated compounds takes place efficiently via a radical mechanism. Upon irradiation with a xenon lamp through Pyrex (hnu >300 nm), terminal alkenes (R-CH=CH2) and alkynes (R-C triple bond CH) undergo iodoperfluoroalkylation with perfluoroalkyl iodides (RF-I) regioselectively, providing R-CH(I)-CH2-RF and R-C(I)=CH-RF, respectively. In the case of terminal allenes (R-CH=C=CH2), the photoinduced iodoperfluoroalkylation occurs selectively at the terminal double bond, giving the corresponding beta-perfluoroalkylated vinylic iodides (R-CH=C(I)-CH2-RF) in good yields. The photoinitiated reaction of vinylcyclopropanes (c-C3H5-C(R)=CH2) with RF-I proceeds via the rearrangement of cyclopropylcarbinyl radical intermediates to the homoallylic radical intermediates, and the corresponding 1,5-iodoperfluoroalkylated products (I-(CH2)2CH=C(R)-CH2-RF) are obtained in high yields. Isocyanides (R-NC), as C-N unsaturated compounds, also undergo the xenon-lamp-irradiated iodoperfluoroalkylation to provide the corresponding 1,1-adducts (R-N=C(I)-RF) in good yields. Furthermore, the present photoinitiation procedure can be applied to the iodotrifluoromethylation of unsaturated compounds, when the xenon-lamp-irradiated reactions are conducted under the refluxing conditions of excess CF3-I.
Keywords:
本文献已被 PubMed 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号