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Barbier reaction

Reaction in organic chemistry

Barbier reaction
Summary

Reaction in organic chemistry

issue = 48}}</ref> In contrast, Grignard reagents and [[organolithium reagent]]s are highly moisture sensitive and must be used under an inert atmosphere without the presence of water. The Barbier reaction is named after [[Philippe Barbier]], who was [[Victor Grignard]]'s teacher.

Scope

Examples of Barbier reactions are the reaction of propargylic bromide with butanal with zinc metal (The attached reference details that the reaction goes to completion after the addition of saturated aqueous ammonium chloride):

Barbier reaction

the intramolecular Barbier reaction with samarium(II) iodide:

Barbier reaction

the reaction of an allyl bromide with formaldehyde in THF with indium powder:

Barbier reaction

The reaction of 3-Bromocyclohexene with benzaldehyde and zinc powder in water:

Barbier reaction

Asymmetric variants

Main article: Asymmetric addition of dialkylzinc compounds to aldehydes

The synthesis of (+)-aspicillin, starts first with a hydroboration, then transmetallation to zinc which can then do an addition into the aldehyde substituent.

The total synthesis of (+)-aspicillin involves a Barbier reaction

References

References

  1. Barbier, P.. (1899). "Synthèse du diéthylhepténol". Compt. Rend..
  2. (1996). "Aqueous Barbier-Grignard type reaction: scope, mechanism, and synthetic applications". Tetrahedron.
  3. (2001). "Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution". [[Molecules (journal).
  4. (2001). "Preparation of oxo-substituted α-chloro ethers and their reaction with samarium diiodide". [[Arkivoc]].
  5. George D. Bennett and [[Leo A. Paquette]]. "Methyl 3-(hydroxymethyl)-4-methyl-2-methylenepentanoate".
  6. (2001). "Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction". [[Molecules (journal).
  7. (1995). "Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal ester". Tetrahedron Letters.
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