Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters
(Chemical Equation Presented) An oxidation exercise: An aerobic alcohol oxidation coupled with a regioselective palladium-catalyzed reductive functionalization of styrenes and arylboronic esters has been developed (see scheme). The mechanism is thought to proceed by initial oxidation of the solvent to generate a PdII-hydride species, which subsequently reacts with the alkene and arylboronic ester to ultimately generate a new C-C bond.
Iwai, Yasumasa,Gligorich, Keith M.,Sigman, Matthew S.
p. 3219 - 3222
(2008/12/23)
Fast Thermal Breaking and Formation of a B - N Bond in 2-(Aminomethyl)benzeneboronates
The title compounds 1 to 6 (Table 1) are shown by 1H, 11B, and 15N NMR shifts to form an intramolecular B-N bond which, according to 1H and 13C NMR, is frequently broken (ΔGc* = 40 to 54 kJ/mol, Table 2) and re-formed.