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Synthesis 2015; 47(03): 289-305
DOI: 10.1055/s-0034-1379884
DOI: 10.1055/s-0034-1379884
review
Recent Developments in the Chemistry of Heteroaromatic N-Oxides
Further Information
Publication History
Received: 01 September 2014
Accepted after revision: 23 October 2014
Publication Date:
14 January 2015 (online)
Abstract
Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon–carbon triple bonds and in regioselective C–H functionalizations of the heteroarene, are contemporary topics of interest and the focus of the discussion.
1 Introduction
2 Synthesis of Heteroaromatic N-Oxides
2.1 Direct Oxidation of Hindered Heteroarenes
2.2 Through Construction of Heteroaromatic Rings
3 Heteroaromatic N-Oxides as Oxidants
3.1 Alkyne Oxidation
3.2 Allene Oxidation
3.3 Carbene Oxidation
4 Heteroaromatic N-Oxides as Substrates
4.1 Deoxygenative ortho-C–H Functionalization with Prior Activation
4.2 Deoxygenative ortho-C–H Functionalization with Nonstabilized Carbanions
4.3 Nondeoxygenative C–H Functionalization
4.3.1 ortho-C–H Functionalization
4.3.2 N-Oxide Directed ortho-Alkyl C–H Functionalization
4.3.3 N-Oxide Directed Remote C–H Functionalization
4.4 1,3-Dipolar Cycloaddition
5 Conclusion and Outlook
-
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