A titanium-catalyzed formal dihydroacylation of terminal alkynes is reported. The new process, in which the alkynes are directly converted into saturated aryl ketones, is based on an initial regioselective hydroaminoalkylation with a secondary benzylamine, a subsequent double bond isomerization of the initially formed allylamine, and a final imine hydrolysis. The entire hydroaminoalkylation-hydrolysis sequence proceeds smoothly with variously substituted Nbenzylanilines, but is limited to terminal alkynes without propargylic hydrogen atoms.
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Thye et al. (Tue,) studied this question.
www.synapsesocial.com/papers/69d894326c1944d70ce051e2 — DOI: https://doi.org/10.1055/a-2849-7288
Hermann Thye
Johanna Holberg
Sven Doye
Synthesis
Carl von Ossietzky Universität Oldenburg
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