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Iridium‐Catalyzed CH Activation versus Directed ortho Metalation: Complementary Borylation of Aromatics and Heteroaromatics
Author(s) -
Hurst Timothy E.,
Macklin Todd K.,
Becker Maike,
Hartmann Eduard,
Kügel Wolfgang,
ParisienneLa Salle JeanChristophe,
Batsanov Andrei S.,
Marder Todd B.,
Snieckus Victor
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000401
Subject(s) - borylation , metalation , electrophile , chemistry , iridium , moiety , catalysis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , aryl , alkyl
Systematic studies are presented demonstrating the complementarity of directed ortho metalation (D o M) and Ir‐catalyzed strategies for the provision of borylated aromatics and their subsequent Suzuki–Miyaura coupling reactions. A new concept, the use of the TMS group, readily introduced by D o M, as a latent regiodirective moiety to overcome the otherwise problematic production of isomeric borylated product mixtures is presented. Additional electrophile‐induced ipso ‐deborylation and D o M reactions of the Bpin products are described.