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An Efficient Iron‐Catalyzed Carbon–Carbon Single‐Bond Cleavage via Retro‐Claisen Condensation: A Mild and Convenient Approach to Synthesize a Variety of Esters or Ketones
Author(s) -
Biswas Srijit,
Maiti Sukhendu,
Jana Umasish
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.201000128
Subject(s) - chemistry , claisen condensation , annulation , catalysis , bond cleavage , organic chemistry , carbon–carbon bond , claisen rearrangement , condensation reaction , inert gas , triple bond , adduct , carbon fibers , michael reaction , combinatorial chemistry , double bond , materials science , composite number , composite material
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.