Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes

Luis J. Benítez-Puebla, Julio López, Marcos Flores-Álamo, David Cruz Cruz, Eduardo Peña-Cabrera, Francisco Delgado, Joaquín Tamariz, Miguel A. Vázquez

Research output: Contribution to journalArticle

Abstract

The results of a study of the reactivities of alkynyl Fischer carbenes in the syntheses of diazaborinine derivatives 7a-i are reported. The strategy employed included the use of β-amino-α,β-unsaturated carbenes (3a–j) with different amines in order to determine the scope of a previously unknown catalytic reaction in the presence of copper salts and anilines. The reaction was highly stereoselective, yielding (Z)-isomers of the β-amino-1-azadiene framework as the main products (4a–o). As an extension of this research, the compounds 4a–o proved to be suitable precursors for the syntheses of diazaborinine scaffolds in good yields (7a-i).

Original languageEnglish
Pages (from-to)6571-6578
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number38
DOIs
StatePublished - 17 Oct 2019

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carbenes
Aniline Compounds
platforms
synthesis
aniline
Scaffolds
Isomers
Amines
Copper
amines
isomers
reactivity
Salts
salts
Derivatives
copper
products
carbene

Keywords

  • Alkynyl Fischer carbenes
  • Diflourodiazaborinine
  • β-Amino carbenes
  • β-Amino-1-azadiene

Cite this

Benítez-Puebla, L. J., López, J., Flores-Álamo, M., Cruz, D. C., Peña-Cabrera, E., Delgado, F., ... Vázquez, M. A. (2019). Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes. European Journal of Organic Chemistry, 2019(38), 6571-6578. https://doi.org/10.1002/ejoc.201901047
Benítez-Puebla, Luis J. ; López, Julio ; Flores-Álamo, Marcos ; Cruz, David Cruz ; Peña-Cabrera, Eduardo ; Delgado, Francisco ; Tamariz, Joaquín ; Vázquez, Miguel A. / Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 38. pp. 6571-6578.
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Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes. / Benítez-Puebla, Luis J.; López, Julio; Flores-Álamo, Marcos; Cruz, David Cruz; Peña-Cabrera, Eduardo; Delgado, Francisco; Tamariz, Joaquín; Vázquez, Miguel A.

In: European Journal of Organic Chemistry, Vol. 2019, No. 38, 17.10.2019, p. 6571-6578.

Research output: Contribution to journalArticle

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AU - Benítez-Puebla, Luis J.

AU - López, Julio

AU - Flores-Álamo, Marcos

AU - Cruz, David Cruz

AU - Peña-Cabrera, Eduardo

AU - Delgado, Francisco

AU - Tamariz, Joaquín

AU - Vázquez, Miguel A.

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