title: Boron-catalyzed silylative reduction of quinolines: selective sp3 C-Si bond formation.
abstract: A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp(3))-Si bond exclusively β to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp(3))-Si bond-forming step from the 1,4-adduct is facile.
authors.affiliation: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) , Daejeon 305-701, South Korea.
authors.forename: Narasimhulu
authors.initials: N
authors.lastname: Gandhamsetty
authors.forename: Seewon
authors.initials: S
authors.lastname: Joung
authors.forename: Sung-Woo
authors.initials: SW
authors.lastname: Park
authors.forename: Sehoon
authors.initials: S
authors.lastname: Park
authors.forename: Sukbok
authors.initials: S
authors.lastname: Chang