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Facile Synthesis and Isolation of Secondary Amines via a Sequential Titanium(IV)‐Catalyzed Hydroamination and Palladium‐Catalyzed Hydrogenation
Author(s) -
Lui Erica K. J.,
Schafer Laurel L.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500861
Subject(s) - chemistry , hydroamination , palladium , catalysis , imine , enamine , alkyl , aryl , organic chemistry , amine gas treating , combinatorial chemistry
An atom economical and catalytic route for the synthesis of aryl‐ and alkyl‐substituted secondary amines has been developed. Using a bis(amidate)bis(amido)titanium(IV) precatalyst, the hydroamination of terminal alkynes with a range of amines results in the selective formation of the anti‐Markovnikov product. The crude enamine/imine mixtures are effectively hydrogenated using palladium on carbon (Pd/C) and H 2 to afford the corresponding secondary amine in excellent yields. Simple work‐up procedures allow for the isolation of pure compounds while avoiding purification via column chromatography.