Photoredox-mediated remote C(sp 3 )–H heteroarylation of free alcohols

We report an efficient and economical method for remote δ C(sp 3 )–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermedi...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 10; no. 3; pp. 688 - 693
Main Authors Li, Guo-Xing, Hu, Xiafei, He, Gang, Chen, Gong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.01.2019
Royal Society of Chemistry
Subjects
Alcohol
Aliphatic alcohols
Aliphatic compounds
Chemistry
Chemistry, Multidisciplinary
Iodine
Photoredox catalysis
Physical Sciences
Science & Technology
FUNCTIONALIZATION
REAGENT
CATALYSIS
MINISCI REACTION
ALKYLATION
GENERATION
RADICALS
EFFICIENT
CARBOXYLIC-ACIDS
DECARBOXYLATIVE ALKYNYLATION
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Summary:We report an efficient and economical method for remote δ C(sp 3 )–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C–C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.
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ISSN:2041-6520
2041-6539
DOI:10.1039/C8SC04134B