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Fluoride‐Triggered Domino Reactions Involving Ammonium Acetylides and Carbonyl Compounds
Author(s) -
Tejedor David,
LópezTosco Sara,
MéndezAbt Gabriela,
GarcíaTellado Fernando
Publication year - 2010
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.200901082
Subject(s) - chemistry , autocatalysis , fluoride , catalysis , domino , organic chemistry , base (topology) , ammonium , inorganic chemistry , mathematical analysis , mathematics
We describe the use of tetrabutylammonium fluoride as a basic trigger for reactions capable of generating structurally diverse products from methyl propiolate and carbonyl derivatives. The processes are based on either chemodifferentiating multicomponent ABB′ three‐component reactions or bimolecular domino reactions, and they operate through three different and well‐defined autocatalytic cycles. These catalytic cycles share a common property: they are launched by the acid–base reaction of fluoride ions to give catalytic amounts of acetylide or enolate salts, but they are maintained by the autocatalytic generation of these salts.