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Synthesis 2021; 53(20): 3836-3846
DOI: 10.1055/a-1516-7917
DOI: 10.1055/a-1516-7917
paper
Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles
We gratefully acknowledge the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Scientific and Technologic Infrastructure of Suzhou (No. SZS201207), and the National Natural Science Foundation of China (No. 21072143) for financial support.
Abstract
The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.
Key words
ytterbium(II) reagent - nucleophilic reagent - single electron transfer reagent - isatin derivatives - 3-substituted 2-oxindolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1516-7917.
- Supporting Information
Publication History
Received: 16 April 2021
Accepted after revision: 25 May 2021
Accepted Manuscript online:
25 May 2021
Article published online:
23 June 2021
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19 Preparation of (2-methylallyl)ytterbium(II) bromide: 3-bromo-2-methylpropene (0.11 mL, 1.1 mmol), Yb powder (0.173 g, 1 mmol) in anhydrous THF (5 mL) and a catalytic amount of I2 were mixed under a nitrogen atmosphere at room temperature. The mixture was stirred for 2 h to obtain a deep-purple solution.
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