What question did this study set out to answer?

To develop a titanium-catalyzed method for converting terminal alkynes into saturated aryl ketones.

April 10, 2026

Titanium-Catalyzed Formal Dihydroacylation of Terminal Alkynes

Key Points

To develop a titanium-catalyzed method for converting terminal alkynes into saturated aryl ketones.
Employs titanium catalyst for a formal dihydroacylation reaction.
Involves regioselective hydroaminoalkylation with secondary benzylamines.
Incorporates double bond isomerization of the allylamine intermediate.
Concludes with imine hydrolysis to yield final products.
Effectively converts various N-benzylanilines with terminal alkynes.
Demonstrates smooth reaction progress without propargylic hydrogen limitations.
Produces saturated aryl ketones as primary products.

Abstract

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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Institutions

Carl von Ossietzky Universität Oldenburg

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