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The Tertiary Sulfonamide as a Latent Directed‐Metalation Group: Ni 0 ‐Catalyzed Reductive Cleavage and Cross‐Coupling Reactions of Aryl Sulfonamides with Grignard Reagents
Author(s) -
Milburn Robert R.,
Snieckus Victor
Publication year - 2004
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.200352633
Subject(s) - aryl , reagent , metalation , chemistry , sulfonamide , alkyl , catalysis , medicinal chemistry , hydride , cleavage (geology) , combinatorial chemistry , grignard reagent , organic chemistry , geotechnical engineering , fracture (geology) , engineering , hydrogen
A mild method for the Ni 0 ‐catalyzed hydrodesulfamoylation (see scheme, B) of aryl sulfonamides ( 1 → 2 ) with i Pr 2 Mg or i PrMgCl as β‐hydride transfer sources can be linked with directed ortho metalation (A and C) to give meta‐ substituted aromatics 2 . Cross‐coupling process with alkyl and aryl Grignard reagents furnish disubstituted benzenes and bi‐ and teraryl compounds.