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Preparation of 1,3-Dienyl Organotrifluoroborates and Their Diels-Alder/Cross Coupling Reactions

Welker, Mark E.

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title
Preparation of 1,3-Dienyl Organotrifluoroborates and Their Diels-Alder/Cross Coupling Reactions
author
De, Subhasis
author
Day, Cynthia S.
author
Welker, Mark E.
abstract
2-BF3 substituted 1,3-butadienes with potassium and tetrabutyl ammonium counterions have been prepared in gram quantities from chloroprene via a simple synthetic procedure. The potassium salt of this new main group element substituted diene has been characterized by 1 H, 13 C, 11 B and 19 F NMR and the tetra n-butyl ammonium salt was also characterized by X-ray crystallography. Diels-Alder reactions of these dienes with dienophiles such as ethyl acrylate, methyl vinyl ketone, and N-phenyl maleimide are reported as well as subsequent Pd catalyzed cross coupling reactions of those Diels-Alder adducts. 4-Phenyl-2-BF3 -substituted-1,3-diene was prepared by magnesium halogen exchange from the corresponding 2-bromo and iodo dienes. The 4-phenyl-2-bromo-1,3-butadiene was also characterized by X-ray crystallography. 4-Phenyl-2-BF3 -1,3-butadiene was used in Diels-Alder/cross coupling reactions and the product of a Diels-Alder reaction with N-Phenylmaleimide followed by cross coupling with 4-bromo-benzonitrile was also characterized by X-ray crystallography.
citation
63 (volume)
date
2011-08-29T18:20:32Z (accessioned)
2011-08-29T18:20:32Z (available)
2007 (issued)
identifier
De S, Day C, Welker ME. Preparation of 1,3-Dienyl Organotrifluoroborates and Their Diels-Alder/Cross Coupling Reactions, Tetrahedron (2007), doi: 10.1016/j.tet.2007.08.063. (citation)
http://hdl.handle.net/10339/36127 (uri)
source
Tetrahedron
http://dx.doi.org/10.1016/j.tet.2007.08.063 (uri)
type
Article

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