Tetramethylammonium Fluoride Alcohol Adducts for S_NAr Fluorination.

ABSTRACT: Nucleophilic aromatic fluorination (S_NAr) is among the most common methods for the formation of C(sp²)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me₄NF·ROH) as fluoride sources for S_NAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me₄NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for S_NAr fluorination under mild an

SUBMITTER: Morales-Colon MT 

PROVIDER: S-EPMC8826451 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature