NDLI: Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones

Content Provider	Royal Society of Chemistry (RSC)
Author	Bortolini, Olga Giovannini, Pier Paolo Pacifico, Salvatore Massi, Alessandro Fantin, Giancarlo Fogagnolo, Marco
Copyright Year	2011
Abstract	An efficient method for the N-heterocyclic carbene (NHC)-catalyzed conjugate addition of acetyl anions to various α,β-unsaturated acceptors (Stetter reaction) has been optimized by using 2,3-butandione (biacetyl) as an alternative surrogate of acetaldehyde. The disclosed procedure proved to be compatible with microwave dielectric heating for reaction time reduction and with the use of different linear α-diketones as acyl anion donors (e.g.3,4-hexanedione for propionyl anion additions). Moreover, the unprecedented umpolung reactivity of cyclic α-diketones in the atom economic nucleophilic acylation of chalcones is herein presented. Mechanistic aspects of the thiazolium-based catalysis involving linear and cyclic α-diketone substrates are also discussed.
Starting Page	8437
Ending Page	8444
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob06480k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Chalconoid Umpolung Persistent carbene Dielectric heating Nucleophilic conjugate addition Microwave Ion Stetter Diacetyl Acetaldehyde Acylation
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones