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 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.
Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6 Canada.
Timothy E
TE
Hurst
Todd K
TK
Macklin
Maike
M
Becker
Eduard
E
Hartmann
Wolfgang
W
Kügel
Jean-Christophe
JC
Parisienne-La Salle
Andrei S
AS
Batsanov
Todd B
TB
Marder
Victor
V
Snieckus
D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006860:Hydrogen Bonding; D007495:Iridium / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001896:Boron Compounds; D006571:Heterocyclic Compounds; D006841:Hydrocarbons, Aromatic; D008670:Metals; D007495:Iridium