Aryl(trimethoxyphenyl)iodonium tosylates have shown potent reactivity for coupling with nucleophiles through inimitable mechanistic pathways. Extension of the reactivity profile of Aryl(TMP)iodonium tosylates to include aryne formation has been achieved by regioselective aromatic C-H deprotonation followed by the chemoselective departure of the iodonium moiety. Control over competing reaction pathways has been achieved by the use of a compatible base centered on aryl electronic properties. Additional insight into the effects of the aryl substituent position is elucidated by one-pot competition experiments. A diverse range of aryl(TMP)iodonium tosylates (20 examples) and arynophiles (5 examples) is presented, as well as a telescoped synthesis of a biologically active compound directly from the aryliodide.

Aryne extrusion from aryl(TMP)iodonium tosylates: Scope, applications, and controlling reaction pathways

ACS Spring Meeting 2021

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