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Synthesis 2018; 50(04): 821-830
DOI: 10.1055/s-0036-1591744
DOI: 10.1055/s-0036-1591744
paper
Photoredox Synthesis of Arylhydroxylamines from Carboxylic Acids and Nitrosoarenes
D.L. thanks the European Union for a Career Integration Grant (PCIG13-GA-2013-631556) and EPSRC for a research grant (EP/P004997/1).Further Information
Publication History
Received: 03 November 2017
Accepted after revision: 01 December 2017
Publication Date:
02 January 2018 (online)
Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry
Abstract
Hydroxylamines are found in biologically active compounds and serve as building blocks for the preparation of nitrogen-containing molecules. Here the direct conversion of carboxylic acids into the corresponding alkylhydroxylamines using organo-photoredox catalysis is reported. The process relies in the generation of alkyl radicals via photoinduced oxidation-decarboxylation and their following reaction with nitrosoarenes. We have successfully applied this method to the late-stage modification of complex and biologically active acids and applied it in novel radical cascade processes.
Key words
hydroxylamines - radical addition - nitrosoarenes - late-stage functionalization - radical cascade - photoredoxSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591744.
- Supporting Information
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