Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of seve...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 16; pp. 6324 - 6329
Main Authors Thakore, Ruchita R, Takale, Balaram S, Casotti, Gianluca, Gao, Eugene S, Jin, Henry S, Lipshutz, Bruce H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2020
Amer Chemical Soc
Subjects
amination
catalytic activity
Chemistry
Chemistry, Organic
chemoselectivity
drugs
hydrophobicity
imines
micelles
palladium
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
NANOPARTICLES
KETONES
SURFACTANT
CHEMISTRY
ALDEHYDES
METAL
PPM LEVELS
MIYAURA CROSS-COUPLINGS
WATER
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Summary:Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c02156