Metal Free Bi-(hetero)aryl Synthesis via Benzyne Truce-Smiles Rearrangement

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Abstract

A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce–Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.

Bibliographical metadata

Original languageEnglish
Pages (from-to)2450-2453
JournalAngewandte Chemie (International Edition)
Volume55
DOIs
StatePublished - 13 Jan 2016