Synthesis of Hindered Biaryls via Aryne Addition and in Situ Dimerization

Benzynes generated under Knochel conditions from 2-iodophenylsulfonates and i PrMgCl smoothly add to thiol, selenol, and amine nucleophiles. Treatment of the resulting aryl Grignard intermediate with a copper salt and an organic oxidant then affords symmetrical biaryls in good yield. 3-Substituted a...

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Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (11), p.2649-2651
Main Authors: García-López, José-Antonio, Çetin, Meliha, Greaney, Michael F.
Format: Article
Language:English
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Summary:Benzynes generated under Knochel conditions from 2-iodophenylsulfonates and i PrMgCl smoothly add to thiol, selenol, and amine nucleophiles. Treatment of the resulting aryl Grignard intermediate with a copper salt and an organic oxidant then affords symmetrical biaryls in good yield. 3-Substituted arynes undergo regioselective addition, enabling synthesis of atropisomeric biaryls with chelating S, Se, or N groups in the 2,2′ positions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01115