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

Gautam Kumar, Debkanta Bhattacharya, Parag Mistry and Indranil Chatterjee*

*Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab 140001, India, Email: indranil.chatterjeeiitrpr.ac.in

G. Kumar, D. Bhattarcharya, P. Mistry, I. Chatterjee, J. Org. Chem., 2023, 88, 6987-6994.

DOI: 10.1021/acs.joc.3c00272

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Abstract

In the presence of catalytic InBr₃, readily available 1,3-benzodioxole and residual H₂O can be used as hydrogen gas surrogate for the hydrogenation of aromatic as well as aliphatic 1,1-di- and trisubstituted alkenes. Deuterium incorporation is enabled by varying the source of the starting deuterated 1,3-benzodioxole or D₂O.

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proposed mechanism

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Key Words

hydrogenation

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ID: J42-Y2023