Ph3P-I-2 mediated aryl esterification with a mechanistic insight

In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I-2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. P-31 NMR st...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 19; pp. 2087 - 2089
Main Authors Phakhodee, Wong, Duangkamol, Chuthamat, Pattarawarapan, Mookda
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 11.05.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
PHOSPHINE
INVOLVEMENT
Phosphorus
Carboxylic acids
TETRATHIOMOLYBDATE
THIOESTERS
TRIPHENYLPHOSPHINE
Esterification
MITSUNOBU REACTION
Phenols
ANHYDRIDES
Iodine
CARBOXYLIC-ACIDS
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Summary:In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I-2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. P-31 NMR studies revealed that the formation of an aryloxyphosphonium salt is crucial in governing the reaction path toward the formation of phenolic esters. (C) 2016 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2016.03.105