Solid-Phase Photochemical Decarboxylative Hydroalkylation of Peptides

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Solid-Phase Photochemical Decarboxylative Hydroalkylation of Peptides

Elkhalifa, Mahmoud; Elbaum, Michael B; Chenoweth, David M; Molander, Gary A

Organic letters, 11/2021, Volume: 23, Issue: 21

Journal Article

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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Elkhalifa, Mahmoud | Elbaum, Michael B | Chenoweth, David M | Molander, Gary A

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