Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation

The bromination of hydrocarbons with CBr4 as a bromine source, induced by light-emitting diode (LED) irradiation, has been developed. Monobromides were synthesized with high efficiency without the need for any additives, catalysts, heating, or inert conditions. Action and absorption spectra suggest...

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Main Authors: Yuta Nishina, Bunsho Ohtani, Kotaro Kikushima
Format: Article
Language:English
Published: Beilstein-Institut 2013-08-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.9.190
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author Yuta Nishina
Bunsho Ohtani
Kotaro Kikushima
author_facet Yuta Nishina
Bunsho Ohtani
Kotaro Kikushima
author_sort Yuta Nishina
collection DOAJ
description The bromination of hydrocarbons with CBr4 as a bromine source, induced by light-emitting diode (LED) irradiation, has been developed. Monobromides were synthesized with high efficiency without the need for any additives, catalysts, heating, or inert conditions. Action and absorption spectra suggest that CBr4 absorbs light to give active species for the bromination. The generation of CHBr3 was confirmed by NMR spectroscopy and GC–MS spectrometry analysis, indicating that the present bromination involves the homolytic cleavage of a C–Br bond in CBr4 followed by radical abstraction of a hydrogen atom from a hydrocarbon.
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spelling doaj.art-7faedd0cc43b4081af76f87ad91869fc2022-12-21T20:20:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-08-01911663166710.3762/bjoc.9.1901860-5397-9-190Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiationYuta Nishina0Bunsho Ohtani1Kotaro Kikushima2Research Core for Interdisciplinary Science, Okayama University, Tsushimanaka, Kita-ku, Okayama 700-8530, JapanCatalysis Research Center, Hokkaido University, Sapporo 001-0021, JapanResearch Core for Interdisciplinary Science, Okayama University, Tsushimanaka, Kita-ku, Okayama 700-8530, JapanThe bromination of hydrocarbons with CBr4 as a bromine source, induced by light-emitting diode (LED) irradiation, has been developed. Monobromides were synthesized with high efficiency without the need for any additives, catalysts, heating, or inert conditions. Action and absorption spectra suggest that CBr4 absorbs light to give active species for the bromination. The generation of CHBr3 was confirmed by NMR spectroscopy and GC–MS spectrometry analysis, indicating that the present bromination involves the homolytic cleavage of a C–Br bond in CBr4 followed by radical abstraction of a hydrogen atom from a hydrocarbon.https://doi.org/10.3762/bjoc.9.190brominationfree radicalhydrocarbonlight-emitting diodephoto irradiation
spellingShingle Yuta Nishina
Bunsho Ohtani
Kotaro Kikushima
Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
Beilstein Journal of Organic Chemistry
bromination
free radical
hydrocarbon
light-emitting diode
photo irradiation
title Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
title_full Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
title_fullStr Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
title_full_unstemmed Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
title_short Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation
title_sort bromination of hydrocarbons with cbr4 initiated by light emitting diode irradiation
topic bromination
free radical
hydrocarbon
light-emitting diode
photo irradiation
url https://doi.org/10.3762/bjoc.9.190
work_keys_str_mv AT yutanishina brominationofhydrocarbonswithcbr4initiatedbylightemittingdiodeirradiation
AT bunshoohtani brominationofhydrocarbonswithcbr4initiatedbylightemittingdiodeirradiation
AT kotarokikushima brominationofhydrocarbonswithcbr4initiatedbylightemittingdiodeirradiation