A chemoselective reduction of alkynes to (E)-alkenes.
The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in clean hydrosilylation to give only the (Z)-trans addition product at ambient temperature with catalyst loadings of 1-5 mol %. The crude vinylsilane products are then protodesilylated by the action of cuprous iodide and TBAF at rt-35 degrees C. The reaction is compatible with many sensitive functional groups and provides a general trans-alkyne reduction not possible by other means.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Ball
Zachary T
ZT
Jöge
Thomas
T
D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D010084:Oxidation-Reduction
D000475:Alkenes; D000480:Alkynes