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
scimago Q1
wos Q1
SJR: 13.441
CiteScore: 59.4
Impact factor: 51.7
ISSN: 23973358
PubMed ID:
37118094
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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Metrics
56
Total citations:
56
Citations from 2024:
43
(76%)