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DOI: 10.1055/s-0037-1612105
Halotrimethylsilane-Nitrite/Nitrate Salts: Efficient and Versatile Reagent System for Diverse Organic Synthetic Transformations
Publication History
Received: 17 December 2018
Accepted: 04 January 2019
Publication Date:
19 March 2019 (online)
Abstract
The reagent system comprised of halotrimethylsilane and nitrite or nitrate salts has now been successfully used as an efficient system for a series of versatile synthetic transformations. In recent years, the significance and efficacy of this system for reactions such as nitration of aromatics and olefins, oxidation of thiols to sulfonyl chlorides, ipso-nitrosation/nitration of arylboronic acids, ipso-nitration of α,β-unsaturated carboxylic acids to nitro olefins, etc. have been disclosed. Though the reagent system has not been exploited to its full potential, the reported reactions reveal its advantages as a very safe and convenient system that works under mild conditions. This brief Account reveals various synthetic applications of halotrimethylsilane-nitrite/nitrate salts in organic synthesis hitherto reported.
1 Introduction
2 Reactions Using a Halotrimethylsilane-Nitrate Salt System
2.1 Nitration of Olefins and Aromatics
2.2 One-Pot Preparation of gem-Chloronitroso, gem-Chloronitro, and vic-Dichloro Compounds
2.3 One-Step Conversion of Anilines into Haloarenes
2.4 Deoximation of Aldoximes to Aldehydes and Ketoximes to Ketones
2.5 One-Pot Synthesis of Cyclic/Noncyclic α-Nitroketones from Cyclic/Noncyclic Olefins
2.6 ipso-Nitration of Arylboronic Acids
2.7 ipso-Nitrosation of Arylboronic Acids
2.8 Oxidation of Sulfides and Sulfoxides to Sulfones
2.9 Oxidative Chlorination of Thiols and Disulfides to Sulfonyl Chlorides
2.10 α-Halogenation of Carbonyl Compounds
2.11 Decarboxylative ipso-Nitration and Dibromination of Cinnamic Acid
3 Conclusion
