A formal enone α-arylation
is described. This metal-free
transformation relies on the I(III)-mediated skeletal reorganization
of silyl enol ethers and features mild conditions, good yields, and
high stereoselectivities for β-substituted enones.
We report the development
of an isothiouronium salt as a reagent
for the operationally simple synthesis of cyanomethyl thioesters with
high functional group tolerance and avoiding the use of thiols. Additionally,
we show that the products can be engaged in amide synthesis in either
a two-step or one-pot fashion.
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