Rare Earth Amide-Catalyzed Direct Thioesterification of Aldehydes with Thiols under Mild Conditions

Nadia Ismaeel; Sajid Imran; Xuehua Zhu; Jue Chen; Dan Yuan; Yingming Yao

doi:10.1021/acs.orglett.3c03497

Rare Earth Amide-Catalyzed Direct Thioesterification of Aldehydes with Thiols under Mild Conditions

Org Lett. 2023 Dec 8;25(48):8672-8676. doi: 10.1021/acs.orglett.3c03497. Epub 2023 Nov 22.

Authors

Nadia Ismaeel¹, Sajid Imran¹, Xuehua Zhu², Jue Chen³, Dan Yuan¹, Yingming Yao¹

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, People's Republic of China.
² School of Chemistry and Life Science, Suzhou University of Science and Technology, Suzhou 215009, People's Republic of China.
³ School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.

PMID: 37991481
DOI: 10.1021/acs.orglett.3c03497

Abstract

Direct thioesterification of aldehydes with thiols catalyzed by readily accessible rare earth/lithium amide RE[N(SiMe₃)₂]₃(μ-Cl)Li(THF)₃ is developed, which enables the preparation of a range of thioesters (31 examples) under room temperature and solvent-free conditions, without using any additive or external oxidant. This method provides a straightforward and atom-efficient approach for the thioester synthesis.