Electron-Transfer Photoredox Catalysis: Development of a Tin-Free Reductive Dehalogenation Reaction

Jagan M. R. Narayanam, Joseph W. Tucker and Corey R. J. Stephenson*

*Department of Chemistry, Boston University, Boston, Massachusetts 02215, Email: crjstephbu.edu

J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J. Am. Chem. Soc., 2009, 131, 8756-8757.

DOI: 10.1021/ja9033582

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Abstract

An operationally simple, tin-free reductive dehalogenation system allows the reduction of activated C-X bonds in good yields with excellent functional-group tolerance and chemoselectivity over aryl and vinyl C-X bonds in the presence of the well-known visible-light-activated photoredox catalyst Ru(bpy)₃Cl₂ in combination with iPr₂NEt and HCO₂H or Hantzsch ester as the hydrogen atom donor.

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Key Words

Dehalogenations, Hantzsch Ester, Formic Acid

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ID: J48-Y2009-1950