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N‐Heterocyclic Carbene Catalysed Oxidative Coupling of Aldehydes with Alcohols/Thiols and One‐Pot Oxidation/Esterification of Allylic Alcohols
Author(s) -
Ji Miran,
Wang Xi,
Lim Yu Na,
Kang YeWon,
Jang HyeYoung
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301337
Subject(s) - chemistry , allylic rearrangement , nucleophile , carbene , dehydrogenation , organic chemistry , oxidative phosphorylation , catalysis , oxidative coupling of methane , alcohol oxidation , medicinal chemistry , biochemistry
A versatile carbene‐catalysed oxidation protocol involving N‐heterocyclic carbene catalysts and 2,2,6,6‐tetramethylpiperidine N ‐oxyl (TEMPO) is described for the synthesis of esters, cinnamic acids, and thioesters. A wide range of esters, thioesters, and cinnamic acids were obtained by metal‐free coupling of aldehydes with aliphatic, allylic and aromatic alcohols, benzyl mercaptan, and water. In addition to the oxidative coupling of aldehydes with nucleophiles, dehydrogenation of saturated aldehydes and oxidation of allylic alcohols were found under our oxidative coupling conditions. Unlike other TEMPO‐mediated oxidative esterification reactions, this reaction does not proceed through a TEMPO ester intermediate to form esters and thioesters.