Free Radical–Mediated Chemoselective Reduction of Enones

Abstract

A novel methodology has been devised for the chemoselective reduction of enones involving the use of ⁿ Bu₃SnH and azobisisobutyronitrile. The 1,4-reduction of variously substituted α,β-unsaturated cyclic and acyclic enones has been successfully carried out under free radical reaction conditions. The reaction has been determined to proceed via single-electron transfer.

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GRAPHICAL ABSTRACT

Keywords:

• AIBN
• ⁿ Bu₃SnH
• chemoselectivity
• enone
• reduction
• SET mechanism

ACKNOWLEDGMENTS

The authors are obliged to the Higher Education Commission, Government of Pakistan, for generous support of a research project (HEC 20-809), a fellowship to Aeysha Sultan (074-141-Ps4-435), IRSIP award and financial assistance for ESIMS, EIMS, and NMR analyses. The authors are also grateful to the Department of Physics, University of Sargodha for the single-crystal XRD facility.