In-Catalyzed Transfer Hydrogenation and Regioselective Hydrogen-Deuterium Addition to the Olefins
Gautam Kumar1, Debkanta Bhattacharya1, Parag Mistry1
1Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab 140001, India.
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.
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