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C 70 Fullerene‐Catalyzed Metal‐Free Photocatalytic ipso ‐Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols
Author(s) -
Kumar Inder,
Sharma Ritika,
Kumar Rakesh,
Kumar Rakesh,
Sharma Upendra
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701573
Subject(s) - chemistry , hydroxylation , aryl , imine , catalysis , phenols , photocatalysis , oxygen , amine gas treating , organic chemistry , photochemistry , combinatorial chemistry , alkyl , enzyme
Abstract A metal‐free C 70 fullerene‐catalyzed method has been developed for the ipso ‐hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C 70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18 O‐labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule. Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one‐pot two‐step process.