Tampere University of Technology

TUTCRIS Research Portal

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

Research output: Contribution to journalArticleScientificpeer-review

Details

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

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)

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

Field of science, Statistics Finland