Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes

25 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we report the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/π-activation mechanism, in contrast to the migratory insertion/cis-trans isomerization pathway that is predominantly observed with other transition metals, in order to afford products with anti-selective installation of the incoming functionalities. Mechanistic insights include several control experiments, NMR studies, HR-MSMS analyses, and DFT calculations that strongly support the proposed mechanism.

Keywords

Alkynes
Gold
Dicarbofunctionalization
Redox Catalysis
DFT Studies

Supplementary materials

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