Late-Stage Diversification of Peptides via Pd-Catalyzed Site-Selective δ-C(sp²)-H Fluorination and Amination

Pd-Catalyzed Picolinamide-Directed C(sp2)–H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates

“…All required materials were purchased from commercial suppliers and used without further purification. The compounds 1a–g , , 1h , 1j , 1w–z , , 1ac , 1al – am , 2c , and 2e–i , were synthesized by following the literature reported procedure. All the heating reactions were carried out over a magnetic stirrer with a hot plate using heating blocks.…”

“…Therefore, the chemical modification of peptides to build engineered nonproteogenic peptide derivatives is the outmost research interest in peptide chemistry and chemical biology for the development of peptide-based therapeutic drugs . As a result, significant progress toward amino acid and peptide modifications has been documented using the traditional cross-coupling approach, and most recently directed C–H activation strategy. , In this arena, transition-metal-catalyzed C­(sp 3 )–H bond functionalization of amino acids and peptides via directing group (DG) assistance is well studied, − while exploration of aryl moiety functionalization of phenylalanine/tyrosine remains relatively limited. − As of our latest understanding, the directed C­(sp 2 )–H sulfonylation of aromatic ring of amino acids and peptides remains an area yet to be explored. Therefore, a catalytic and site-selective procedure for the synthesis of sulfonylated amino acids and peptides is highly required.…”

Backbone-enabled modification of peptides with benzoquinone via palladium-catalyzed δ-C(sp2)–H functionalization

“…16 a Furthermore, we efficiently achieved fluorination of Phe residues with the assistance of the PA group. 16 b Nevertheless, conventional external group-assisted strategies necessitate additional steps for the incorporation and removal of directing groups. In contrast, backbone amides within peptides serve as internal bidentate directional groups to facilitate C–H activation, presenting a compelling approach to streamline the process.…”

Pd-Catalyzed Picolinamide-Directed C(sp2)-H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates

“…8,9 In this arena, transition-metal-catalyzed C(sp 3 )-H bond functionalization of amino acids and peptides via directing group (DG) assistance are well studied, [10][11][12] while exploration of aryl moiety functionalization of phenylalanine/tyrosine remains relatively limited. [13][14][15][16] As of our latest understanding, the directed C(sp 2 )-H sulfonylation of aromatic ring of amino acids and peptides remains an area yet to be explored. Therefore, a catalytic and site-selective procedure for the synthesis of sulfonylated amino acids and peptides is highly required.…”