Insights into Substrate Self-Assisted Activation of Allylic Alcohols Guiding to Mild Allylic Substitution of Tautomerizable Heteroarenes

A substrate self-assisted activation of allylic alcohols by tautomerizable heteroarenes via hydrogen bonding was disclosed by various NMR techniques, including variable-temperature 1H NMR, Job plot, and 1H NMR titration. Guided by these finding, a much milder allylic substitution of tautomerizable heteroarenes with allylic alcohols was developed, affording the target products in high yields.