Application of vinyl tris(trimethylsilyl)germanes in Pd-catalyzed couplings.
The oxidative treatment of vinyltris(trimethylsilyl)germanes with hydrogen peroxide (NaOH/H(2)O/THF) or tert-butyl peroxide (KH/THF) generates reactive germanol or germanoxane species that undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides and aryl triflates in the presence of Pd(PPh(3))(4). Vinylgermanes having either a conjugated or isolated double bond serve as versatile transmetalation reagents. The E-germanes undergo coupling with retention of stereochemistry under aqueous and anhydrous conditions, while coupling of Z-germanes occurs with less stereoselectivity to produce a mixture of E/Z products.
Wang
Zhizhong
Z
Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA.
Wnuk
Stanislaw F
SF
D002384:Catalysis; D005857:Germanium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D009942:Organometallic Compounds; D012821:Silanes; D014753:Vinyl Compounds; D005857:Germanium; D010165:Palladium