Telescopic Synthesis of Triazol‐4‐yl Modified Phenylalanine Conjugates and Peptide Modification Using a Sonogashira Domino Strategy at Room Temperature

We report a telescopic two‐step synthetic strategy for efficiently constructing [1 H ]‐1,2,3‐triazol‐4‐yl modified phenylalanine conjugates. The method combines Sonogashira coupling and a one‐pot domino reaction involving desilylation, azidation, and click chemistry. This protocol enhances the potential for peptide modification and facilitates the synthesis of polyazide derivatives that can be suitable for dendrimeric cores. This reaction yields good results and provides a scalable route, successfully accommodating a wide range of aromatic and heteroaromatic methyl bromides, while achieving excellent chiral integrity and 100% 1,4‐regioselectivity. We also explored the application of a 1,4‐disubstituted [1 H ]‐1,2,3‐triazol‐4‐yl phenylalanine conjugate as a directing group for C(sp 2 )‐H di‐halogenation.