Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13674-13679Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01798
Keywords
-
Categories
Funding
- National Science Foundation under Chemical Innovation Center for Selective C-H Functionalization [CHE-1700982]
- Center for Rapid Online Analysis of Reactions (ROAR) at Imperial College London [EPSRC] [EP/R008825/1]
- EPSRC [EP/R008825/1] Funding Source: UKRI
Ask authors/readers for more resources
Mechanistic investigations uncover a novel role for 2-pyridone ligands and interrogate the origin of enantioselectivity in the (+)-norbornene-mediated Pd-catalyzed meta-C(aryl)-H functionalization of diarylmethylamines. Observations from kinetic analysis in concert with in situ F-19 NMR monitoring allow us to propose that the pyridone ligand plays a role in enhancing the rate- and enantio-determining insertion of an arylpalladium species into a chiral norbornene derivative. The unprecedented features of 2-pyridone ligands in asymmetric 1,2 migratory insertion, and norbornene as a transient chiral mediator in relay chemistry, provide new insights into this ligand scaffold for future developments in stereoselective transition-metal-catalyzed C-H functionalization.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available