Communication
doi.org/10.1002/ejoc.202001238
EurJOC
European Journal of Organic Chemistry
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In summary, a general methodology for the synthesis of
α-iodomethyl ketones has been developed via NHC-based
Au-catalyzed hydration of 1-iodoalkynes. By using a low loading
of a well-defined Au(I)-NHC catalyst under mild conditions, the
protocol presents good selectivity and provides good to excel-
lent isolated yields for a variety of aromatic substrates. These
compounds can also be prepared from terminal alkynes by
means of a sequential Au-catalyzed iodination/hydration proto-
col. The versatility of this approach is highlighted in the
straightforward access to arylketone derivatives by simply per-
forming sequential hydration/functionalization reactions, owing
to the robustness of the catalytic system. Several examples have
been presented, broadening the applicability of Au-NHC cata-
lysts in modern synthesis involving alkynes and 1-iodoalkynes.
These results are an important step towards milder, faster and
more efficient/sustainable synthetic routes.
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The authors gratefully acknowledge Syngenta (studentship to
AGH), the UGent BOF (starter grant) and the FWO for funding.
Keywords: Gold · N-heterocyclic carbenes · Iodination ·
Hydration · Sequential
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