Site-Selective Modification of Peptides via Late-Stage Pd-Catalyzed Tandem Reaction of Phenylalanine with Benzoquinone

An efficient and straightforward approach for site-selectivefunctionalizationof phenylalanine and phenylalanine-containing peptide via a Pd-catalyzedtandem reaction has been developed. The robust method underwent dualC-H activation, including C-C coupling with benzoquinoneand intramolecular C-N cyclization, providing a feasible andrapid synthetic route to incorporate 4-benzoquinone-indoline fragmentsinto peptides.

Automated summary

An efficient and straightforward approach for site-selective functionalization of phenylalanine and phenylalanine-containing peptide has been developed via a Pd-catalyzed tandem reaction. The method allows for dual C-H activation, including C-C coupling with benzoquinone and intramolecular C-N cyclization, providing a rapid and feasible synthetic route to incorporate 4-benzoquinone-indoline fragments into peptides.