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Mechanistic study demonstrates peptide modification via deprotonated amide activation, indicating broad applicability.
Herein, we have discovered a unique deprotonated amide activation of dehydroalanine and developed a remote functionalization reaction of the double bond under mild conditions. The reaction exhibits good chemoselectivity and site-selectivity and is compatible with different kinds of peptides. Mechanistic studies first disclose in situ generated electron-rich enamine after deprotonation of amide hydrogen in Dha, followed by an intermolecular charge transfer process between the enamine and diaryliodonium salt.
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Wang et al. (2026) studied this question.
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