Cascade Aryne Aminoarylation for Biaryl Phenol Synthesis

Aniruddha Das, Danielle L. Myers, Venkataraman Ganesh, Michael Greaney

Research output: Contribution to journalArticlepeer-review

Abstract

We describe a transition metal-free approach to hindered 3-amino-2-aryl phenols through nucleophilic addition –Smiles-Truce rearrangement of a functionalized Kobayashi aryne precursor. Under anionic conditions, secondary alkyl amines add to the aryne intermediate to set up an aryl transfer from a neighboring sulfonate group. The use of a sulfonate, rather than the more typical sulfonamide, enables access to phenolic biaryl products that are important motifs in natural products and pharmaceuticals.
Original languageEnglish
JournalOrganic Letters
Publication statusAccepted/In press - 15 Mar 2024

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