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

作者：Biswas Srijit; Maiti Sukhendu; Jana Umasish^*

来源：European Journal of Organic Chemistry, 2010, (15): 2861-2866.

DOI：10.1002/ejoc.201000128

• Iron
• Nucleophilic addition
• Cleavage reactions
• Esters
• Ketones

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.

• 出版日期2010-5