Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.
[reaction: see text] Ruthenium-catalyzed alkyne hydrosilylation or silyl-alkyne Alder ene reactions provide entry into benzyldimethylsilyl (BDMS)-substituted alkenes. The BDMS-vinylsilanes are further elaborated through mild palladium-catalyzed cross coupling and show significant stability to intervening synthetic operations, including silyl ether deprotection.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Machacek
Michelle R
MR
Ball
Zachary T
ZT
D000475:Alkenes / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents; D013058:Mass Spectrometry; D010165:Palladium / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000475:Alkenes; D001593:Benzyl Compounds; D003432:Cross-Linking Reagents; D012821:Silanes; D014753:Vinyl Compounds; C476908:benzyldimethylsilyl; C476909:vinylsilane; D010165:Palladium; D012428:Ruthenium