An efficient photoinduced iodoperfluoroalkylation of carbon-carbon unsaturated compounds with perfluoroalkyl iodides

The Journal of Organic Chemistry
Kaname TsuchiiAkiya Ogawa

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 t...Continue Reading

Citations

Jan 6, 2017·The Journal of Organic Chemistry·Zhong-Quan Liu, Dong Liu
Jul 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kohei MatsuzakiNorio Shibata
Jun 19, 2018·Chemical Communications : Chem Comm·Redouane BeniazzaJean-Marc Vincent
Aug 15, 2012·Angewandte Chemie·Armido Studer
Jun 26, 2014·Angewandte Chemie·Hiromichi Egami, Mikiko Sodeoka
Nov 11, 2018·Chemistry : a European Journal·Massimo BrochettaDebabrata Maiti
Mar 23, 2019·Chemical Society Reviews·Paramasivam SivaguruXihe Bi
Sep 27, 2019·Chemical Communications : Chem Comm·Erlin ZhuChun-Yang He
Mar 27, 2015·Chemistry : a European Journal·Jian LeiQiang Zhu
Jul 13, 2012·Chemistry : a European Journal·Anne Miersch, Gerhard Hilt
Jul 27, 2012·Angewandte Chemie·Yi Li, Armido Studer
May 10, 2017·Organic & Biomolecular Chemistry·Jing-Jing Ma, Wen-Bin Yi
Apr 21, 2018·Chemical Science·Guojiao Wu, Axel Jacobi von Wangelin
Dec 28, 2012·Journal of the American Chemical Society·Takashi KippoIlhyong Ryu
Aug 14, 2019·Organic Letters·Liang ZhaoChun-Yang He
May 24, 2013·Organic Letters·Shuhei SuminoIlhyong Ryu
Apr 24, 2015·Organic Letters·Jian LeiQiang Zhu
Aug 15, 2019·The Journal of Organic Chemistry·Oleg V FedorovAlexander D Dilman

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