Solid-Phase Photochemical Decarboxylative Hydroalkylation of Peptides

The compatibility of photochemistry with solid-phase peptide synthesis is demonstrated via photochemical hydroalkylation to form C­(sp3)–C­(sp3) bonds between on-resin Giese acceptors and redox-active esters. Both iridium-based photocatalysts and Hantszch ester led to high yields, with final reactio...

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Published inOrganic letters Vol. 23; no. 21; pp. 8219 - 8223
Main Authors Elkhalifa, Mahmoud, Elbaum, Michael B, Chenoweth, David M, Molander, Gary A
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 05.11.2021
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Summary:The compatibility of photochemistry with solid-phase peptide synthesis is demonstrated via photochemical hydroalkylation to form C­(sp3)–C­(sp3) bonds between on-resin Giese acceptors and redox-active esters. Both iridium-based photocatalysts and Hantszch ester led to high yields, with final reaction conditions producing full conversions within 30 min under ambient conditions. The chemistry is compatible with a broad range of peptide side chains, redox-active esters, and resin. These conditions represent the first example of photochemical peptide modifications on resin.
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M.A.E. and M.B.E. contributed equally.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c02928