期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 29, 页码 8431-8434出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603222
关键词
arynes; cycloaddition; hypervalent compounds; regioselectivity; synthetic methods
资金
- Portland State University
- American Chemical Society Petroleum Research Fund (PRF DNI1) [54405]
Described here is an efficient method to access highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts. The iodonium salts are prepared in a single pot from either commercially available aryl iodides or arylboronic acids. The aryne intermediates are generated by ortho-C-H deprotonation of aryl(mesityl)iodonium salt with a commercially available amide base and trapped in a cycloaddition reaction with furan in moderate to good yields. Coupling partners for the aryne intermediates beyond furan are also described, including benzyl azide and alicyclic amine nucleophiles. The regio- and chemoselectivity of this reaction is discussed and evidence for the spectator aryl ligand of the iodonium salt as a critical control element in selectivity is presented.
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