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A General Strategy Toward Aromatic 1,2‐Ambiphilic Synthons: Palladium‐Catalyzed ortho ‐Halogenation of PyDipSi‐Arenes
Author(s) -
Dudnik Alexander S.,
Chernyak Natalia,
Huang Chunhui,
Gevorgyan Vladimir
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201004426
Subject(s) - synthon , halogenation , aryl , palladium , electrophile , chemistry , nucleophile , iodide , combinatorial chemistry , silanes , organic chemistry , electrophilic addition , catalysis , silane , medicinal chemistry , alkyl
A general and efficient strategy to synthesize 1,2‐ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium‐catalyzed directed ortho ‐halogenation of aryl silanes (see scheme; Py=2‐pyridyl). The usefulness of these 1,2‐ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.