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CC BY 4.0 · Synthesis 2022; 54(21): 4683-4689
DOI: 10.1055/a-1840-5483
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α-C–H Photoalkylation of a Glucose Derivative in Continuous Flow

Marc L. M. C. Mouthaan
a   Department of Chemical Biology, Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands
,
Kees Pouwer
b   Symeres B.V., Kadijk 3, 9747 AT Groningen, The Netherlands
,
Mark L. G. Borst
b   Symeres B.V., Kadijk 3, 9747 AT Groningen, The Netherlands
,
Martin D. Witte 
a   Department of Chemical Biology, Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands
,
Adriaan J. Minnaard  ∗
a   Department of Chemical Biology, Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands
› Author AffiliationsThis work is supported by the Carbohydrate Competence Center’s (CCC) ‘CarboBased’ program.
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Abstract

Site-selective photoalkylation is a powerful strategy to extend the carbon framework of carbohydrates, otherwise often attainable only through laborious syntheses. This work describes the adaptation and upscaling of the photoalkylation of a glucose derivative as a continuous flow process. The reported iridium catalyst is replaced by an organic sensitizer and the reaction has been carried out on 40-gram scale.

Key words

C–H functionalization - photoredox catalysis - carbohydrates - flow chemistry - hydrogen atom transfer - radicals

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1840-5483.
  • Supporting Information


Publication History

Received: 20 March 2022

Accepted after revision: 28 April 2022

Accepted Manuscript online:
02 May 2022

Article published online:
14 June 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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