<scp>Palladium‐Catalyzed Methionine‐Facilitated</scp> β and γ C(sp<sup>3</sup>)–H Arylation of <scp>N‐Terminal</scp> Aliphatic Amino Acids of Peptides
Xiangxiang Chen, Bo Li, Huarong Tong, Liping Qi, Gang He, Gong Chen
Abstract
Comprehensive Summary A new method for post‐assembly modification of peptides via the Pd‐catalyzed endogenous group‐directed sp 3 C—H arylation with aryl iodides is developed. The sulfide side chain of methionine (Met) residue can facilitate the arylation of both β and γ methyl C—H bonds of N‐terminal aliphatic amino acids of peptides via formation of 5 or 6‐membered palladacycle intermediates. The reactions can proceed in moderate to good yield and with excellent diastereoselectivity.
Topics & Concepts
ChemistryMethionineAmino acidCatalysisResidue (chemistry)ArylYield (engineering)PalladiumStereochemistryOrganic chemistryBiochemistryAlkylMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsFluorine in Organic Chemistry