Nature Reviews Chemistry, volume 6, issue 11, pages 782-805
Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation
Publication type: Journal Article
Publication date: 2022-09-21
Journal:
Nature Reviews Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 36.3
ISSN: 23973358
General Chemistry
General Chemical Engineering
Abstract
Photoredox catalysis has recently emerged as a powerful synthetic platform for accessing complex chemical structures through non-traditional bond disconnection strategies that proceed through free-radical intermediates. Such synthetic strategies have been used for a range of organic transformations; however, in carbohydrate chemistry they have primarily been applied to the generation of oxocarbenium ion intermediates in the ubiquitous glycosylation reaction. In this Review, we present more intricate light-induced synthetic strategies to modify native carbohydrates through homolytic C–H and C–C bond cleavage. These strategies allow access to glycans and glycoconjugates with profoundly altered carbohydrate skeletons, which are challenging to obtain through conventional synthetic means. Carbohydrate derivatives with such structural motifs represent a broad class of natural products integral to numerous biochemical processes and can be found in active pharmaceutical substances. Here we present progress made in C–H and C–C bond activation of carbohydrates through photoredox catalysis, focusing on the operational mechanisms and the scope of the described methodologies. Photoredox catalysis has emerged as an indispensable platform for de novo synthesis and modification of complex biologically relevant molecules. This Review highlights photoredox-mediated C–H and C–C bond activation of carbohydrates leading to non-conventional C-functionalized sugars and rare sugar isomers.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Shatskiy A. et al. Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation // Nature Reviews Chemistry. 2022. Vol. 6. No. 11. pp. 782-805.
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Shatskiy A., Stepanova E., Kärkäs M. D. Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation // Nature Reviews Chemistry. 2022. Vol. 6. No. 11. pp. 782-805.
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TY - JOUR
DO - 10.1038/s41570-022-00422-5
UR - https://doi.org/10.1038%2Fs41570-022-00422-5
TI - Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation
T2 - Nature Reviews Chemistry
AU - Shatskiy, Andrey
AU - Stepanova, Elena
AU - Kärkäs, Markus D
PY - 2022
DA - 2022/09/21 00:00:00
PB - Springer Nature
SP - 782-805
IS - 11
VL - 6
SN - 2397-3358
ER -
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@article{2022_Shatskiy,
author = {Andrey Shatskiy and Elena Stepanova and Markus D Kärkäs},
title = {Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation},
journal = {Nature Reviews Chemistry},
year = {2022},
volume = {6},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1038%2Fs41570-022-00422-5},
number = {11},
pages = {782--805},
doi = {10.1038/s41570-022-00422-5}
}
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Shatskiy, Andrey, et al. “Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation.” Nature Reviews Chemistry, vol. 6, no. 11, Sep. 2022, pp. 782-805. https://doi.org/10.1038%2Fs41570-022-00422-5.