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

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

doi:10.1002/ejoc.200900056

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 journal › Article › Scientific › peer-review

76 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 language	English
Pages (from-to)	1859-1863
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.200900056
Publication status	Published - Apr 2009
Externally published	Yes
Publication type	A1 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

Access to Document

10.1002/ejoc.200900056

Cite this

@article{948f1d5aa8b74bbb9b5e0d3f7988c68d,

title = "Water: A Suitable Medium for the Petasis Borono-Mannich Reaction",

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",

author = "Candeias, {Nuno R.} and Veiros, {Luis F.} and Afonso, {Carlos A. M.} and Gois, {Pedro M. P.}",

year = "2009",

month = apr,

doi = "10.1002/ejoc.200900056",

language = "English",

pages = "1859--1863",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "12",

}

TY - JOUR

T1 - Water: A Suitable Medium for the Petasis Borono-Mannich Reaction

AU - Candeias, Nuno R.

AU - Veiros, Luis F.

AU - Afonso, Carlos A. M.

AU - Gois, Pedro M. P.

PY - 2009/4

Y1 - 2009/4

N2 - 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)

AB - 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)

KW - Boron

KW - Water chemistry

KW - Multicomponent reactions

KW - Amines

KW - Solvent effects

KW - DIELS-ALDER REACTIONS

KW - ALPHA-AMINO-ACIDS

KW - C-H INSERTION

KW - AQUEOUS-MEDIA

KW - MULTICOMPONENT REACTIONS

KW - ORGANIC-REACTIONS

KW - 3-COMPONENT REACTION

KW - ORGANOBORONIC ACIDS

KW - HETEROCYCLES

KW - SOLVENT

U2 - 10.1002/ejoc.200900056

DO - 10.1002/ejoc.200900056

M3 - Article

SN - 1434-193X

SP - 1859

EP - 1863

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this