INOR 127

C(sp³)-N Bond-forming reductive elimination of benzylamines from benzyl palladium amido complexes

Devon C. Rosenfeld, devon.rosenfeld@yale.edu and John F. Hartwig, john.hartwig@yale.edu. Department of Chemistry, Yale University, New Haven, CT 06520-8107

Reductive eliminations to form C-N bonds involving an sp³-hybridized carbon are rare. To observe this process, a series of tri-tert-butyl phosphine ligated palladium benzyl diarylamido complexes was synthesized. Thermolysis of ^tBu₃Pd(Bn)(NAr₂) led to formation of N-benzyl diarylamine in low yield. However, replacement of tri-tert-butyl phosphine by bidentate phosphine ligands (DPEphos, BINAP and DPPF) resulted in the formation of bisphosphine palladium benzyl amido complexes. These complexes underwent reductive elimination yielding N-benzylamine in moderate to excellent yield. The mechanism of the C-N bond formation will be discussed.

Organometallic: Synthesis
1:30 PM-4:50 PM, Sunday, 10 September 2006 Moscone Center -- Room 310, Oral

Division of Inorganic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006