Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 15, Pages 2861-2866Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000128
Keywords
Iron; Nucleophilic addition; Cleavage reactions; Esters; Ketones
Categories
Funding
- Department of Chemistry, Jadavpur University
- University Grants Commission (UGC), New Delhi, India
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An efficient iron-salt-catalyzed carbon-carbon bond cleavage occurring through a retro-Claisen condensation reaction has been developed. The reaction is useful for the synthesis of a variety of esters or ketones under mild conditions. This method works under solvent-free conditions without the need of an inert atmosphere. This protocol is also applicable for the one-pot syntheses of ketones through tandem carbon-carbon bond formation (substitution or Michael) followed by a retro-Claisen reaction. However, for Michael adducts, ring annulation takes place subsequently. Notably, this method is very simple, convenient, high yielding, and only a catalytic (5 to 10 mol-%) amount of Fe(OTf)(3) is needed.
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