4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 7, Pages 2450-2453

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510236

Keywords

arynes; biaryls; heterocycles; rearrangements; synthetic methods

Funding

  1. Engineering and Physical Sciences Research Council [1758870, 1357470] Funding Source: researchfish

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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.

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