Beilstein J. Org. Chem.2013,9, 621–627, doi:10.3762/bjoc.9.69
Chemical Technology, Shenyang 110142, People’s Republic of China 10.3762/bjoc.9.69 Abstract Low-valency titanium species, generated in situ by using Ti(OiPr)4/2 c-C5H9MgCl reagent, react with imines to give a titanium-iminecomplex that can couple with terminal alkynes to provide azatitanacyclopentenes
undergoes an unexpected 1,3-amino migration on silica gel during the column chromatography.
Keywords: allylic amine; azatitanacyclopentene; reductive cross-coupling; regioselectivity; terminal alkyne; titanium-iminecomplex; Introduction
Allylic amines are fundamental three-carbon building blocks in
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Graphical Abstract
Scheme 1:
Titanium-mediated cross-coupling of imines with terminal alkynes.