Tryptophan Bioconjugation through Auxiliary Boron-Accelerated, Additive-Free Friedel-Crafts Alkylation.

ABSTRACT: Chemical tools have allowed the interrogation of molecular events in biological systems through the realization of additive-free labeling approaches such as strain-promoted chemistry. Although design and synthesis of strained compounds remain challenging tasks, efforts to identify an alternative chemical strategy to achieve such additive-free labeling are lacking. Serendipitously, we found that a trifluoroborate unit can act as an auxiliary group to enable the additive-free Friedel-Crafts alkylation reaction at room temperature in the potentially protein-compatible solvent hexafluoroisopropanol (HFIP) without any additional catalysts such as a Lewis acidic metal and a Brønsted acid. The structure-reactivity relationship of a set of thiophene electrophiles for the dehydrative alkylation of

SUBMITTER: Uzoewulu CP 

PROVIDER: S-EPMC12848692 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature