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Synthesis 2022; 54(23): 5192-5202
DOI: 10.1055/a-1922-8846
DOI: 10.1055/a-1922-8846
feature
Transition-Metal-Free N-Arylation of N-Methoxysulfonamides and N,O-Protected Hydroxylamines with Trimethoxyphenyliodonium (III) Acetates
This work was partially supported by JSPS KAKENHI grant numbers 19K05466 (T.D.) and 18H02014 (K.K.) and JST CREST grant number JPMJCR20R1. T.D. also acknowledges support from the Ritsumeikan Global Innovation Research Organization (R-GIRO) project.
Abstract
Trimethoxyphenyliodonium(III) acetate [TMP-iodonium(III) acetate] functions as an efficient arylation reagent for N,O-protected hydroxylamines, generating aniline derivatives in the absence of transition metal catalysts. Various N-methoxysulfonamides participated in the amination reaction to produce the corresponding N-methoxysulfonylanilines. This amination reaction was compatible with several protecting groups, including Troc (2,2,2-trichloroethoxycarbonyl), Cbz (benzyloxycarbonyl), Boc (tert-butoxycarbonyl), benzyl, acetyl, and silyl groups. This method uses TMP-iodonium(III) acetate and efficiently synthesizes various aniline derivatives that are versatile synthetic intermediates for functional organic molecules.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1922-8846.
- Supporting Information
Publication History
Received: 05 July 2022
Accepted after revision: 11 August 2022
Accepted Manuscript online:
11 August 2022
Article published online:
23 September 2022
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For copper-catalyzed [1,3] methoxy rearrangement of N-methoxyamide, see: