Work

Alkyl and Aryl Thioester Synthesis via N-Heterocyclic Carbene-Catalyzed α-Thio Aldehyde Rearrangement

Year: 2025

Type: article

Abstract: We have developed a highly atom economic transformation to provide a thioester. The N-heterocyclic carbene-catalyzed rearrangement of α-thio aldehydes affords thioesters in good yields. This reaction exhibits a broad substrate scope and is applicable to aldehydes bearing either alkylthio or arylthio groups. The optimal combination of catalyst precursor and base is highly dependent on the nature of the S substituent in the starting α-thio aldehyde.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04522

Authors: Tatsuya Fujiwara, Tsubasa Inokuma, Ken-ichi Yamada

Institution: Tokushima University

Language: English

Topic: N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Support for Pioneering Research Initiated by the Next Generation, Fugaku Trust for Medicinal Research, University of Tokushima, Japan Society for the Promotion of Science

Awards: G1117236828, G1825857869, G2902931828