1. Academic Validation
  2. Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds

Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds

  • Org Biomol Chem. 2019 Aug 28;17(32):7558-7563. doi: 10.1039/c9ob01568j.
Yuanding Fang 1 Rong Zhao 1 Yuan Yao 2 Yang Liu 2 Denghu Chang 1 Ming Yao 3 Lei Shi 4
Affiliations

Affiliations

  • 1 School of Science, Harbin Institute of Technology, Shenzhen, 518055, China and MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.
  • 2 MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.
  • 3 Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen, 448000, China. lshi@hit.edu.cn.
  • 4 Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen, 448000, China. lshi@hit.edu.cn and School of Science, Harbin Institute of Technology, Shenzhen, 518055, China and MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China and Beijing National Laboratory for Molecular Sciences, Beijing 100190, China.
Abstract

A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding Phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue LIGHT needs to be further studied.

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