Synthesis of CF3-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3 + 2] Cyclization Reaction

Huamin Wang; Wenjing Niu; Yongjun He; Yibo Wei; Xianxian Li; Ying-Wu Lin

doi:10.1021/acs.joc.3c01768

Synthesis of CF₃-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3 + 2] Cyclization Reaction

J Org Chem. 2023 Nov 3;88(21):15282-15287. doi: 10.1021/acs.joc.3c01768. Epub 2023 Oct 12.

Authors

Huamin Wang¹, Wenjing Niu¹, Yongjun He¹, Yibo Wei¹, Xianxian Li¹, Ying-Wu Lin^{1

2

3}

Affiliations

¹ School of Chemistry and Chemical Engineering, University of South China, Hengyang421001,P. R. China.
² Hengyang Medical College, University of South China, Hengyang 421001,P. R. China.
³ Laboratory of Protein Structure and Function, University of South China Medical School, Hengyang421001,P. R. China.

PMID: 37824681
DOI: 10.1021/acs.joc.3c01768

Abstract

We report herein a general and effective system achieving cyclization of β-trifluoromethyl enones with amidines in the presence of 1,3-diiodo-5,5-dimethylhydantoin (DIH), which affords a range of trifluoromethylated 2-imidazolines in synthetically useful yields with good diastereoselectivities (up to 95% yield, up to 98:2 dr) and good functional group tolerance. Furthermore, the one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. More significantly, the reaction mechanism was verified by ESI-MS studies of possible intermediates, and a reasonable reaction mechanism was proposed.