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Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition

Wilfried Raimondi 1 Daniel Dauzonne 2 Thierry Constantieux 1 Damien Bonne 1, * Jean Rodriguez 1 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : -Functionalized furans are very easily synthesized by exploiting the dual nucleophilic character of 1,2-dicarbonyls and the dual electrophilic properties of (2-chloro-2-nitroethenyl)benzenes in a one-pot, formal [3+2] cycloaddition. Using a base (DBU), the desired trisubstituted heterocycles were formed rapidly (10-30 min) in good to excellent yields (51-92 %), and this versatile, metal-free methodology was applied to the synthesis of 2-acyl- and 2-carboalkoxyfurans and furan-2-carboxamides. Additionally, by using 2-ketophosphonate derivatives as dinucleophiles, the corresponding 2-phosphorylfurans were formed in good yields (53-74 %).
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https://hal.archives-ouvertes.fr/hal-00747378
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Submitted on : Wednesday, October 31, 2012 - 11:06:28 AM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Wilfried Raimondi, Daniel Dauzonne, Thierry Constantieux, Damien Bonne, Jean Rodriguez. Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2012, pp.6119-6123. ⟨10.1002/ejoc.201201192⟩. ⟨hal-00747378⟩

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