Resume

• Computational Chemistry

  Physical Chemistry

  Oxidative Functionalization of Benzylic C-H Bonds By DDQ

  Steven J. Konezny

  C–H activation of the methyl group of toluene and related ArCH3 derivatives by 2

  3-dichloro-4

  5-dicyano-1

  4-benzoquinone (DDQ) gives insertion products

  ArCH2O[C6Cl2(CN)2]OH via a rate-determining hydride abstraction by DDQ. The resulting benzylic ether can undergo reactions with phosphines to give benzylic phosphonium salts (Wittig reagents) and with phosphites to give phosphonate esters (Horner–Wadsworth–Emmons reagents).

  Oxidative Functionalization of Benzylic C-H Bonds By DDQ

  Batista

  Yale University

  Yale University