Iridium-catalyzed, substrate-directed C-H borylation reactions of benzylic amines.
The iridium-catalyzed arene C-H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4'-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.
Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcalá Park, San Diego, California 92110, USA.
Andrew J
AJ
Roering
Lillian V A
LV
Hale
Phillip A
PA
Squier
Marissa A
MA
Ringgold
Emily R
ER
Wiederspan
Timothy B
TB
Clark
D000588:Amines / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D001897:Boronic Acids; D004952:Esters; D009942:Organometallic Compounds; D007495:Iridium