Acid-Promoted Amination of Cyclohexenone for the Divergent Synthesis of p-Aminophenols and Tertiary Amines

Li Liu; Jun Li; Ya Chen; Shanping Chen; Fuhong Xiao; Guo-Jun Deng

doi:10.1021/acs.joc.4c00292

Acid-Promoted Amination of Cyclohexenone for the Divergent Synthesis of p-Aminophenols and Tertiary Amines

J Org Chem. 2024 Sep 18. doi: 10.1021/acs.joc.4c00292. Online ahead of print.

Authors

Li Liu¹, Jun Li¹, Ya Chen¹, Shanping Chen¹, Fuhong Xiao¹, Guo-Jun Deng^{1

2}

Affiliations

¹ Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Hunan Province Key Laboratory of Green Organic Synthesis and Application, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
² School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China.

PMID: 39295166
DOI: 10.1021/acs.joc.4c00292

Abstract

A tunable method for the selective preparation of p-aminophenol and tertiary amines from a secondary amine and cyclohexenone has been described. Nonaromatic cyclohexenones were used as an aryl source. The desired tertiary amine products were generated when using I₂ as the catalyst. This approach yields single-site-selective p-aminophenol without using I₂, and the ¹⁸O labeling experiments demonstrated that hydroxyl oxygen originates from O₂.