Photoredox-Catalyzed Sulfonaminoformyloxylation of Alkenes with N-Aminopyridinium Salts and DMF

A photoredox-catalyzed three-component sulfonaminoformyloxylation reaction between alkenes, N-aminopyridinium salts and DMF has been developed, which avoids the usage of erosive formic acid as the formyloxylation reagent. Besides DMF, alkyl and aryl carboxylic acids proved to be feasible nucleophile...

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Published inAdvanced synthesis & catalysis Vol. 366; no. 7; pp. 1517 - 1522
Main Authors Wang, Yue, Liu, Jie, Chen, Zhang, Chen, Jinjin, Peng, Xue, Wang, Zhen, Zeng, Yao-Fu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 09.04.2024
Wiley Subscription Services, Inc
Subjects
Alkenes
Carboxylic acids
Chemistry
Chemistry, Applied
Chemistry, Organic
Esters
Formic acid
Nucleophiles
Physical Sciences
Reagents
Science & Technology
FORMYLOXYLATION
REARRANGEMENT
N,N-DIMETHYLFORMAMIDE
alkene
OLEFINS
N-aminopyridinium salt
RADICALS
AZIRIDINES
photocatalysis
DMF
CHLORINATION
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Summary:A photoredox-catalyzed three-component sulfonaminoformyloxylation reaction between alkenes, N-aminopyridinium salts and DMF has been developed, which avoids the usage of erosive formic acid as the formyloxylation reagent. Besides DMF, alkyl and aryl carboxylic acids proved to be feasible nucleophiles to afford various beta-amino esters. The robustness of this method was further demonstrated by its applicability in the late-stage modification of biological molecules. Control experiments suggested that a sulfonamidyl radical was involved in this reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301446