Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 7, Pages 996-999Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201600083
Keywords
chlorination; laser flash photolysis; photoinduced electron transfer; quinone; radical
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) [26620154, 26288037]
- ALCA project from JST, Japan
- SENTAN project from JST, Japan
- Grants-in-Aid for Scientific Research [16H02268, 26620154, 16K13964, 26288037] Funding Source: KAKEN
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Photochlorination of aromatic substrates by hydrogen chloride with 2,3-dichloro-5,6-cyano-p-benzoquinone (DDQ) occurs efficiently to produce the corresponding monochlorinated products selectively under visible-light irradiation. The yields for the chlorination of phenol were 70% and 18% for p- and o-chlorophenol, respectively, without formation of further chlorinated products. The photoinduced chlorination is initiated by electron transfer from Cl- to the triplet excited state of DDQ. The radical intermediates involved in the photochemical reaction have been detected by time-resolved transient absorption measurements.
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