160567-89-5Relevant articles and documents
Facile Synthesis and Isolation of Secondary Amines via a Sequential Titanium(IV)-Catalyzed Hydroamination and Palladium-Catalyzed Hydrogenation
Lui, Erica K. J.,Schafer, Laurel L.
supporting information, p. 713 - 718 (2016/03/09)
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 H2 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.
Radical cyclisations of imines and hydrazones
Bowman, W. Russell,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
, p. 7959 - 7980 (2007/10/02)
Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.
Cyclisation of Carbinyl Radicals onto Imines and Hydrazones
Bowman, W. Russel,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
, p. 6369 - 6372 (2007/10/02)
The regioselectivity of intramolecular addition of sp3 carbon-centered radicals onto C=N double bonds of imines and hydrazones is influenced by the position and polarisation of the C=N bond.
