Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions

Pufan Ni; Lei Yang; Yi Shen; Lei Zhang; Yueyue Ma; Maolin Sun; Ruihua Cheng; Jinxing Ye

doi:10.1021/acs.joc.2c01133

Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions

J Org Chem. 2022 Oct 7;87(19):12677-12687. doi: 10.1021/acs.joc.2c01133. Epub 2022 Sep 14.

Authors

Pufan Ni¹, Lei Yang¹, Yi Shen¹, Lei Zhang¹, Yueyue Ma², Maolin Sun², Ruihua Cheng², Jinxing Ye^{1

2}

Affiliations

¹ Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
² School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China.

PMID: 36102897
DOI: 10.1021/acs.joc.2c01133

Abstract

A general method for the synthesis of phenols from electron-deficient aryl ammonium salts or heteroaryl ammonium salts under mild conditions was developed. Benzaldehyde oxime, acetohydroxamic acid, and hydroxylamine hydrochloride were investigated as hydroxide surrogates respectively. With these hydroxide surrogates, a series of phenols were prepared in yields of 20-98%.