Transition-state metal aryl bond stability determines regioselectivity in palladium acetate mediated C-H bond activation of heteroarenes.
Density functional calculations reveal that the stability of developing metal aryl bonds in Pd(II)-acetate C-H activation transition states determines regioselectivity in arene and heteroarene compounds. This kinetic-thermodynamic connection explains the general preference for activation of the strongest C-H bond and provides the possibility for regioselectivity prediction.
Department of Chemistry and Biochemistry, Brigham Young University , Provo, Utah 84602, United States.
Alban
A
Petit
Josh
J
Flygare
Alex T
AT
Miller
Gerrit
G
Winkel
Daniel H
DH
Ess
D002384:Catalysis; D006860:Hydrogen Bonding; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D028561:Transition Elements / Q000737:chemistry*
D008670:Metals; D028561:Transition Elements; D010165:Palladium