Highly selective perfluoroalkylchalcogenation of alkynes by the combination of iodoperfluoroalkanes and organic dichalcogenides upon photoirradiation

Vinylic selenides and tellurides are useful synthetic intermediates for preparation of vinylic compounds and carbonyl compounds. Herein we report highly selective perfluoroalkylselenation and -telluration of terminal alkynes by using heteroatom mixed systems, i.e., (PhSe)2/RfI and (PhTe)2/RfI, upon...

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Veröffentlicht in:Tetrahedron 2012-12, Vol.68 (51), p.10516-10522
Hauptverfasser: Tamai, Taichi, Nomoto, Akihiro, Tsuchii, Kaname, Minamida, Yoshiaki, Mitamura, Takenori, Sonoda, Motohiro, Ogawa, Akiya
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container_end_page 10522
container_issue 51
container_start_page 10516
container_title Tetrahedron
container_volume 68
creator Tamai, Taichi
Nomoto, Akihiro
Tsuchii, Kaname
Minamida, Yoshiaki
Mitamura, Takenori
Sonoda, Motohiro
Ogawa, Akiya
description Vinylic selenides and tellurides are useful synthetic intermediates for preparation of vinylic compounds and carbonyl compounds. Herein we report highly selective perfluoroalkylselenation and -telluration of terminal alkynes by using heteroatom mixed systems, i.e., (PhSe)2/RfI and (PhTe)2/RfI, upon photoirradiation. When the reaction of aromatic alkynes and conjugated enynes with diphenyl diselenide and perfluoroalkyl iodide is conducted in benzotrifluoride (BTF) as solvent upon irradiation with a xenon lamp through Pyrex (hν >300 nm), novel perfluoroalkylselenation of the alkynes takes place regio- and stereoselectively to give 1-(perfluoroalkyl)-2-(phenylseleno)alkenes in good yields. Similar procedure can be applied to photoinduced perfluoroalkyltelluration of aromatic alkynes, and perfluoroalkyl and phenyltelluro groups are introduced to the terminal and internal positions of alkynes regio- and stereoselectively. Since perfluoroalkyl (fluorous) groups make it possible to isolate the products easily by fluorous/organic/aqueous extraction technique, the obtained perfluoroalkylselenation and -telluration products are promising as synthetic intermediates. [Display omitted]
doi_str_mv 10.1016/j.tet.2012.09.026
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Herein we report highly selective perfluoroalkylselenation and -telluration of terminal alkynes by using heteroatom mixed systems, i.e., (PhSe)2/RfI and (PhTe)2/RfI, upon photoirradiation. When the reaction of aromatic alkynes and conjugated enynes with diphenyl diselenide and perfluoroalkyl iodide is conducted in benzotrifluoride (BTF) as solvent upon irradiation with a xenon lamp through Pyrex (hν &gt;300 nm), novel perfluoroalkylselenation of the alkynes takes place regio- and stereoselectively to give 1-(perfluoroalkyl)-2-(phenylseleno)alkenes in good yields. Similar procedure can be applied to photoinduced perfluoroalkyltelluration of aromatic alkynes, and perfluoroalkyl and phenyltelluro groups are introduced to the terminal and internal positions of alkynes regio- and stereoselectively. Since perfluoroalkyl (fluorous) groups make it possible to isolate the products easily by fluorous/organic/aqueous extraction technique, the obtained perfluoroalkylselenation and -telluration products are promising as synthetic intermediates. 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Herein we report highly selective perfluoroalkylselenation and -telluration of terminal alkynes by using heteroatom mixed systems, i.e., (PhSe)2/RfI and (PhTe)2/RfI, upon photoirradiation. When the reaction of aromatic alkynes and conjugated enynes with diphenyl diselenide and perfluoroalkyl iodide is conducted in benzotrifluoride (BTF) as solvent upon irradiation with a xenon lamp through Pyrex (hν &gt;300 nm), novel perfluoroalkylselenation of the alkynes takes place regio- and stereoselectively to give 1-(perfluoroalkyl)-2-(phenylseleno)alkenes in good yields. Similar procedure can be applied to photoinduced perfluoroalkyltelluration of aromatic alkynes, and perfluoroalkyl and phenyltelluro groups are introduced to the terminal and internal positions of alkynes regio- and stereoselectively. 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source ScienceDirect Journals (5 years ago - present)
subjects Alkynes
Dichalcogenide
Iodides
Perfluoroalkyl iodide
Perfluoroalkyls
Photoirradiation
Radical reactions
Selenides
Solvents
Terminals
Tetrahedrons
Xenon lamps
title Highly selective perfluoroalkylchalcogenation of alkynes by the combination of iodoperfluoroalkanes and organic dichalcogenides upon photoirradiation
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