Beilstein J. Org. Chem.2024,20, 479–496, doi:10.3762/bjoc.20.43
both within the context of a classic gold π-activation/protodeauration mechanism and a general acid-catalyzed mechanism without intermediate gold alkyls.
Keywords: alkenehydroamination; general acid catalysis; gold catalysis; isotope effect; phosphine ligand effect; solvent effect; Introduction
) protodeauration (Scheme 1), the depth of experimental mechanistic validation achieved for allenes and alkynes have not been reproduced with alkenes. In an important foundational study by Toste, the expected alkylgold intermediate from intramolecular alkenehydroamination was isolated, however, turnover
as the final step of alkenehydroamination, however, an alternative mechanistic model remains elusive.
There are significant similarities between gold- and acid-catalyzed alkene additions, further confounding easy conclusions about the operative mechanism. Early gold-catalyzed alkene hydroaminations
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Graphical Abstract
Scheme 1:
Proposed mechanism and observation of alkylgold intermediates.