Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation

Narasimhulu Gandhamsetty, Seewon Joung, Sung Woo Park, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

Abstract

A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp3)-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(sp3)-Si bond-forming step from the 1,4-adduct is facile.

Original languageEnglish
Pages (from-to)16780-16783
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number48
DOIs
StatePublished - 3 Dec 2014
Externally publishedYes

Fingerprint Dive into the research topics of 'Boron-catalyzed silylative reduction of quinolines: Selective sp<sup>3</sup> C-Si bond formation'. Together they form a unique fingerprint.

Cite this