By applying the “interplay”
mode, which consolidates
two key reactivity modes of gold catalysis, namely π-activation
mode and cross-coupling mode, the first alkynylative Meyer–Schuster
rearrangement is designed and successfully implemented. The current
protocol gives straightforward access to enynones, a highly valuable
building block, from easily available propargyl alcohol feedstocks.
Control experiments suggest an Au(III) catalyst triggers the Meyer–Schuster
rearrangement, whereas monitoring the reaction with ESI-HRMS provided
strong evidence in favor of a key alkynylgold(III) intermediate which
supports the proposed “interplay” scenario.
In recent years, gold catalysis involving Au(I)/Au(III) redox cycle has gained significant attention. This account summarizes our contributions in the development of Au(I)/Au(III) catalysis focusing on cross-coupling reactions and 1,2-difunctionalization reactions of C-C multiple bonds. A special emphasis has been given towards understanding the mechanism of the reactions.
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