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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Boron-catalyzed silylative reduction of quinolines: selective sp3 C-Si bond formation
Narasimhulu Gandhamsetty1, Seewon Joung, Sung-Woo Park
1Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) , Daejeon 305-701, South Korea.
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.
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