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- Title
Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement.
- Authors
Holden, Catherine M.; Sohel, Shariar M. A.; Greaney, Michael F.
- 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.
- Subjects
AROMATIC compound synthesis; HETEROCYCLIC compounds synthesis; TRANSITION metal catalysts; STOICHIOMETRY; BENZYNES; ATROPISOMERS; AMINE synthesis; REARRANGEMENTS (Chemistry)
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 7, p2496
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510236