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

J Org Chem

College of Chemistry and Chemical Engineering, Green Catalysis & Synthesis Key Laboratory of Xinyang City, Xinyang Normal University, Xinyang, Henan 464000, China.

Published: April 2020

A substrate self-assisted activation of allylic alcohols by tautomerizable heteroarenes via hydrogen bonding was disclosed by various NMR techniques, including variable-temperature H NMR, Job plot, and H 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.

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http://dx.doi.org/10.1021/acs.joc.0c00094DOI Listing

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