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

作者：Wu, Xiaoyu; Ding, Guangni; Yang, Liqun; Lu, Wenkui; Li, Wanfang; Zhang, Zhaoguo; Xie, Xiaomin^*

来源：Organic Letters, 2018, 20(18): 5610-5613.

DOI：10.1021/acs.orglett.8b02287

• ACID-DERIVATIVES
• CHEMOSELECTIVE REDUCTION
• CARBONYL-COMPOUNDS
• TERTIARY AMIDES
• HYDROSILANES
• ACTIVATION
• ESTERS
• IMINES
• ISOINDOLES
• ANNULATION

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)(2)MeSiH 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 omega-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.

• 出版日期2018-9-21
• 单位上海交通大学