Iridium-Catalyzed CH Activation versus Directed ortho Metalation: Complementary Borylation of Aromatics and Heteroaromatics

Systematic studies are presented demonstrating the complementarity of directed ortho metalation (DoM) 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 DoM, as a...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-07, Vol.16 (27), p.8155-8161
Main Authors: Hurst, Timothy E., Macklin, Todd K., Becker, Maike, Hartmann, Eduard, Kügel, Wolfgang, Parisienne-La Salle, Jean-Christophe, Batsanov, Andrei S., Marder, Todd B., Snieckus, Victor
Format: Article
Language:English
Subjects:
Activation
Activation analysis
boron
Boron Compounds - chemistry
Catalysis
Chemical reactions
CH activation
deborylation
Heterocyclic Compounds - chemistry
Hydrocarbons, Aromatic - chemistry
Hydrogen Bonding
Iridium - chemistry
metalation
Metals - chemistry
Molecular Structure
Stereoisomerism
Strategy
Suzuki-Miyaura coupling
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Summary:Systematic studies are presented demonstrating the complementarity of directed ortho metalation (DoM) 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 DoM, as a latent regiodirective moiety to overcome the otherwise problematic production of isomeric borylated product mixtures is presented. Additional electrophile‐induced ipso‐deborylation and DoM reactions of the Bpin products are described. DoM versus CH activation: Systematic studies are presented demonstrating the complementarity of directed ortho metalation (DoM) and Ir‐catalyzed strategies for the provision of borylated aromatics and their subsequent Suzuki–Miyaura coupling reactions. A new concept that overcomes the otherwise problematic production of isomeric borylated product mixtures is presented.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201000401