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Straightforward Reductive Esterification of Carbonyl Compounds with Carboxylic Acids through Tosylhydrazone Intermediates
Author(s) -
GarcíaMuñoz AngelHumberto,
TomásGamasa María,
PérezAguilar M. Carmen,
CuevasYañez Erick,
Valdés Carlos
Publication year - 2012
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.201200647
Subject(s) - chemistry , diazo , catalysis , organic chemistry , combinatorial chemistry
The reaction of carboxylic acids with tosylhydrazones in basic media gives rise to the corresponding esters through an O–H insertion reaction in the in situ generated diazo compound. The process is operationally very simple, catalyst free, and very general with regard to the structure of both coupling partners. In particular, the esterification can be accomplished by employing tosylhydrazones derived from enolizable carbonyl compounds. Considering the ready availability of tosylhydrazones from carbonyl compounds, this reaction can be visualized as a reductive esterification of carbonyl compounds.