Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquin...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (18), p.5610-5613
Main Authors: Wu, Xiaoyu, Ding, Guangni, Yang, Liqun, Lu, Wenkui, Li, Wanfang, Zhang, Zhaoguo, Xie, Xiaomin
Format: Article
Language:English
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Summary:An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02287