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Pd-catalyzed site-selective C(sp2)-H radical acylation of phenylalanine containing peptides with aldehydes
Marcos San Segundo1, Arkaitz Correa1
1University of the Basque Country (UPV/EHU) , Department of Organic Chemistry I , Joxe Mari Korta R&D Center, Avda. Tolosa 72 , 20018 Donostia-San Sebastián , Spain .
Abstract:
The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed δ-C(sp2)-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its site-specificity, tolerance of sensitive functional groups, scalability, and enantiospecificity and exhibits entire chemoselectivity for Phe motifs over other amino acid units. The compatibility of this dehydrogenative acylation platform with a number of oligopeptides of high structural complexity illustrates its ample opportunities for the late-stage peptide modification and bioconjugation.
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