Premium
Water: A Suitable Medium for the Petasis Borono‐Mannich Reaction
Author(s) -
Candeias Nuno R.,
Veiros Luís F.,
Afonso Carlos A. M.,
Gois Pedro M. P.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900056
Subject(s) - chemistry , mannich reaction , salicylaldehyde , solvent , boronic acid , organic chemistry , combinatorial chemistry , catalysis , polymer chemistry , schiff base
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)