Radical alkylation of isocyanides with amino acid-/peptide-derived Katritzky salts via photoredox catalysis

An efficient and mild method was developed for the synthesis of 6-alkylated phenanthridines upon visible light irradiation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amino acids/peptides were used as radical precursors for the alkylation of isocyan...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 17; no. 6; pp. 1531 - 1534
Main Authors Zhu, Ze-Fan, Zhang, Miao-Miao, Liu, Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 06.02.2019
Royal Society of Chemistry
Subjects
Alkylation
Amino acids
Catalysis
Chemistry
Chemistry, Organic
Functional groups
Irradiation
Light irradiation
NMR
Nuclear magnetic resonance
Peptides
Photoredox catalysis
Physical Sciences
Pyridinium
Radiation
Salts
Science & Technology
PHENANTHRIDINE
CROSS-COUPLINGS
REDOX-ACTIVE ESTERS
DERIVATIVES
FLUOROALKYLATION
N-HETEROCYCLES
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Summary:An efficient and mild method was developed for the synthesis of 6-alkylated phenanthridines upon visible light irradiation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amino acids/peptides were used as radical precursors for the alkylation of isocyanobiphenyl species. The reaction displays an excellent functional group tolerance and a potential utility for peptide functionalization, allowing access to desired products in good to excellent yields.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02786b