Water: A Suitable Medium for the Petasis Borono-Mannich Reaction

Nuno R. Candeias, Luis F. Veiros, Carlos A. M. Afonso, Pedro M. P. Gois

Research output: Contribution to journalArticleScientificpeer-review

64 Citations (Scopus)

Abstract

Water was used as the solvent in the Petasis borono-Mannich reaction. With the use of salicylaldehyde, secondary amines and boronic acids, several alkylaminophenols were obtained in considerably high yields in water. By using the same methodology, 2H-chromenes were prepared with the use of vinyl boronic acids. The reaction mechanism was studied by DFT calculations, and the results obtained corroborate the solvent effect experimentally observed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Original languageEnglish
Pages (from-to)1859-1863
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number12
DOIs
Publication statusPublished - Apr 2009
Externally publishedYes
Publication typeA1 Journal article-refereed

Keywords

  • Boron
  • Water chemistry
  • Multicomponent reactions
  • Amines
  • Solvent effects
  • DIELS-ALDER REACTIONS
  • ALPHA-AMINO-ACIDS
  • C-H INSERTION
  • AQUEOUS-MEDIA
  • MULTICOMPONENT REACTIONS
  • ORGANIC-REACTIONS
  • 3-COMPONENT REACTION
  • ORGANOBORONIC ACIDS
  • HETEROCYCLES
  • SOLVENT

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