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

Ruchita R. Thakore, Balaram S. Takale*, Gianluca Casotti, Eugene S. Gao, Henry S. Jin and Bruce H. Lipshutz*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: balaram_takaleucsb.edu, bhlipshutzucsb.edu

R. R. Thakore, B. S. Takale, G. Casotti, E. S. Gao, H. S. Jin, B. H. Lipshutz, Org. Lett., 2020, 22, 6324-6329.

DOI: 10.1021/acs.orglett.0c02156 (free Supporting Information)



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Abstract

Reductive amination between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles in water. A broad range of substrates can be converted under mild conditions in the presence of 0.20 mol % Pd/C and triethylsilane, leading to high chemical yields of the desired secondary and tertiary amines.

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Key Words

reductive amination, triethylsilane, green chemistry


ID: J54-Y2020