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

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 rearrangemen...

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Detalles Bibliográficos
Autores principales: Holden, Catherine M., Sohel, Shariar M. A., Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819888/
https://www.ncbi.nlm.nih.gov/pubmed/26762551
http://dx.doi.org/10.1002/anie.201510236
Descripción
Sumario: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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