Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived alpha-amino radicals to carbonyl compounds via visible-light photocatalyst in water

A general and efficient visible-light photoredox-catalysed decarboxylative radical coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of various 1,2-amino alcohols by using water as the solvent at room temperature is described. This protocol is characterised by broad...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 2; pp. 336 - 341
Main Authors Pan, Shulei, Jiang, Min, Hu, Jinjin, Xu, Ruigang, Zeng, Xiaofei, Zhong, Guofu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2020
Royal Society of Chemistry
Subjects
Alcohol
Alcohols
Aldehydes
Amino acids
Aromatic compounds
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Multidisciplinary
Coupling (molecular)
Green & Sustainable Science & Technology
Green chemistry
Ketones
NMR
Nuclear magnetic resonance
Physical Sciences
Room temperature
Science & Technology
Science & Technology - Other Topics
Substrates
MERGING PHOTOREDOX
SHARPLESS ASYMMETRIC AMINOHYDROXYLATION
ARYLATION
SULFOBACIN-B
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
C-H BONDS
PHOTOREDOX CATALYSIS
CARBOXYLIC-ACIDS
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Summary:A general and efficient visible-light photoredox-catalysed decarboxylative radical coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of various 1,2-amino alcohols by using water as the solvent at room temperature is described. This protocol is characterised by broad substrate scopes, mild reaction conditions and amenability to gram-scale synthesis, which opens up a simple, mild but effective method to produce 1,2-amino alcohols from readily available starting materials.
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc03470f