1384216-49-2Relevant academic research and scientific papers
Iridium-catalyzed, substrate-directed C-H borylation reactions of benzylic amines
Roering, Andrew J.,Hale, Lillian V. A.,Squier, Phillip A.,Ringgold, Marissa A.,Wiederspan, Emily R.,Clark, Timothy B.
, p. 3558 - 3561 (2012)
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.
Role of hemilabile diamine ligands in the amine-directed C-H borylation of arenes
Hale, Lillian V. A.,McGarry, Kathryn A.,Ringgold, Marissa A.,Clark, Timothy B.
supporting information, p. 51 - 55 (2015/01/30)
A study of the role played by the bidentate ligand used in amine-directed C-H borylation is described. Both reaction conversion and selectivity were significantly impacted when steric congestion and electronic perturbations of the bidentate diamine ligand were made, but a more significant influence was imparted by reducing the bite angle of the ligand. N-Benzylaminopyridine was identified as a general ligand that improves both selectivity and yield for most problematic substrates previously reported with picolylamine as ligand.
