M.C. White/Q Chen, Chem 153 Q&A-342 Week of december 2. 2002 An interesting synthesis of cyclopropanes has been recently reported by gri Propose a mechanism for this transformation. Pd dba)3, TFP NHMe P KCO3, DMF TFP= 68% NMe NHMe reductive elimination oxidative addition Pdln Attack of amide at central carbon of NMe NAMe Wacker-like process KHCO3 InsertIo CNHMe CO3 NAMe Insertion Attack of nucleophiles at the central carbon of(n-allyl)palladium complexes is much less common than attack at the termini. Central attack results in the formatic of a palladacyclobutane, which in the absence of a good leaving group can undergo reductive elimination to form a cyclopropane and regenerate pd(o) Grigg, R. Eur J. Org. Chem. 2001, 707-712M.C. White/Q. Chen, Chem 153 Q&A -342- Week of December 2, 2002 NMe O Ln Pd K2CO3 NHMe O PdLn I O P PdLn NHMe O I NMe O I NHMe O I NHMe O An interesting synthesis of cyclopropanes has been recently reported by Grigg. Propose a mechanism for this transformation. + Pd2(dba)3, TFP K2CO3, DMF 68% TFP = 3 PdLn insertion Attack of amide at central carbon of the π-allyl is considered to be a Wacker-like process. Grigg, R. Eur. J. Org. Chem. 2001, 707-712. NHMe O PdL2 I NMe O oxidative addition insertion reductive elimination Attack of nucleophiles at the central carbon of (η3-allyl)palladium complexes is much less common than attack at the termini. Central attack results in the formation of a palladacyclobutane, which in the absence of a good leaving group can undergo reductive elimination to form a cyclopropane and regenerate Pd(0). KHCO3 KI