In-Catalyzed Transfer Hydrogenation and Regioselective Hydrogen–Deuterium Addition to the Olefins

Abstract

A unique and valuable methodology is developed for the hydrogenation of aromatic as well as aliphatic 1,1-di- and trisubstituted alkenes. In the presence of catalytic InBr3, readily available 1,3-benzodioxole and residual H2O present in the reaction mixture are utilized as a hydrogen gas surrogate and proved to be a practical source of deuterium incorporation into the olefins on either side by varying the source of the starting deuterated 1,3-benzodioxole or D2O. Experimental studies show the transfer of hydride from 1,3-benzodioxole to the carbocationic intermediate generated from the protonation of alkenes by the H2O–InBr3 adduct remains the critical step.

TfOH-catalyzed transfer hydrogenation reaction using 1-tetralone as a novel dihydrogen source

“…17 These achievements have opened new avenues for the synthesis of complex organic molecules and have the potential to impact various areas of organic chemistry research. 18 One drawback, however, is that the preparation of cyclohexa-1,4-dienes involves a multi-step process.…”