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Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer
Author(s) -
Gujjarappa Raghuram,
Vodnala Nagaraju,
Garg Aakriti,
Hazra Chinmoy K.,
Gupta Sreya,
Malakar Chandi C.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904059
Subject(s) - chemistry , hydroxylation , amino acid , hydrogen peroxide , aryl , histidine , triethylamine , solvent , organic chemistry , combinatorial chemistry , alkyl , biochemistry , enzyme
An efficient amino‐acid‐mediated ipso ‐hydroxylation of arylboronic acids, aryl boronate esters and aryl trifluoroborates to aryl alcohols has been described. The current protocol was realized by using sub‐stoichiometric amount of l ‐histidine in presence of triethylamine under aerobic conditions in DMF as solvent. This amino‐acid‐mediated process provides an alternative route for the hydroxylation of organoborons through in situ generation of hydrogen peroxide. The present protocol explores the synthetic utility of amino acids as organocatalysts for the preparation of aryl alcohols. It was observed that l ‐histidine plays an important role for the conversion of aerial oxygen in to hydrogen peroxide via thermal excitation process followed by thermal degradation of Et 3 N. The developed approach holds good for a wide range of compounds with excellent yields and competent functional group tolerance.