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Synlett 2017; 28(18): 2396-2400
DOI: 10.1055/s-0036-1588442
DOI: 10.1055/s-0036-1588442
cluster
Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes
This research was supported by the Institute for Basic Science (IBS-R010-D1) in Korea.Further Information
Publication History
Received: 30 March 2017
Accepted after revision: 09 May 2017
Publication Date:
23 May 2017 (online)
Published as part of the Cluster Silicon in Synthesis and Catalysis
Abstract
A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N-oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588442.
- Supporting Information
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