Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones
Literature Information
Publication Date
2023-10-25
DOI
10.1039/D3QO01693E
Impact Factor
5.281
Authors
Yueqiang Liu, Sheng Zhang, Yang Li, Xiaoqiang Yu, Xiujuan Feng, Ming Bao
View Original
Abstract
A new strategy for in situ generation of vinyl cation intermediates from α-diazocarbonyl compounds is described in this paper. The reaction of α-aryl-α-diazoketones with trialkylsilyl triflates proceeded smoothly to produce cyclic silyl enol ethers via vinyl cation intermediates. The cyclic silyl enol ethers obtained were successfully employed as building blocks to prepare a variety of indanones and α,β-unsaturated ketones using FeCl3 and FeCl3·6H2O as oxidants, respectively. The in situ generation of vinyl cation intermediates in the reaction of α-aryl-α-diazoketones with trialkylsilyl triflates was verified by control experiments and DFT calculations.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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