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Graphite/Methanesulfonic Acid (GMA) as a New Reagent for Sulfonylation of Phenols and Thia‐ Fries Rearrangement of Aryl Sulfonates to Sulfonylphenols
Author(s) -
Sharghi Hashem,
ShahsavariFard Zahra
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490295
Subject(s) - chemistry , methanesulfonic acid , fries rearrangement , phenols , sulfonate , aryl , reagent , organic chemistry , phenol , p toluenesulfonic acid , medicinal chemistry , catalysis , alkyl , sodium
A new facile method for direct sulfonylation of phenols was developed. Graphite in methanesulfonic acid (GMA) was used to prepare sulfonylphenols by sulfonylation of phenol and naphthalene derivatives with p ‐toluenesulfonic acid (=4‐methylbenzenesulfonic acid) ( Table 1 ) and the thia‐ Fries rearrangement of aryl sulfonates ( Table 4 ). Mechanistic studies showed that the sulfonylation reaction of phenols in GMA occurred through an initial sulfonate formation followed by a thia‐ Fries rearrangement of the aryl sulfonate by an intermolecular mechanism ( Scheme 3 ).