Deuteration of Alkenes with NaBD4/AcOD in Pre-Sence of Pd on Carbon

Abstract

Activated alkenes such as cinnamates and chalcones can easily be converted to 2,3-dideuterio-arylpropionates and dideuteriochalcones, respectively, by the action of NaBD4, AcOD in the presence of Pd on carbon. Toluene or benzene was used as solvent. It was shown that Pd on carbon was necessary for the reaction to proceed. Deuterium addition experiments were also carried out with NaBD4, AcOD, D2O in the presence of Pd on carbon.

DDQ-Catalyzed Oxidative C(sp3)–H Functionalization of Aryltetralins and Subsequent Chemoselective Oxidative Demethylation to Access Dihydronaphthalenes and Dihydronaphthoquinones

“…The reaction was executed with 3 equiv of DDQ. mediated exhaustive reduction 26 delivered 24 with good stereocontrol.…”

“…Then, the elaboration of acid 19 to ester 20 and amide 21 was also achieved. Further, the selective reduction of the carbonyl group in 2a via the Luche protocol smoothly delivered the allylic alcohol 22 , which was easily elaborated to the methyl ether 23 , while the borohydride-mediated exhaustive reduction delivered 24 with good stereocontrol.…”