Photoinduced Decarboxylative Thioacylation of N‐Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides

• Published in: Chemistry : a European journal Vol. 30; no. 68; pp. e202402716 - n/a
• Main Authors: Wang, Qian, Zhang, Cheng‐Lin, Li, Yan‐Fei, Zhou, Yu‐Jing, Cui, Fei‐Hu, Jiang, Jing‐Chen, Pan, Ying‐Ming, Duan, Wen‐Gui, Tang, Hai‐Tao
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 05.12.2024; Wiley Subscription Services, Inc
• Subjects: Agrochemicals; Biocompatibility; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Decarboxylation; Decarboxylation coupling; Disulfides; Dithiocarbamate compounds; Esters; Functional groups; N-hydroxyphthalimide esters; Natural products; Organic chemistry; Physical Sciences; Science & Technology; Tetraalkylthiuram disulfides; Visible-light-induced; N-hydroxyphthalimide esters; DESIGN; Dithiocarbamate compounds; SULFONYLATION; EFFICIENT SYNTHESIS; Visible-light-induced; Tetraalkylthiuram disulfides; BREAST-CANCER; THIOLS; CROSS-COUPLING REACTIONS; INHIBITION; BIOLOGICAL EVALUATION; AGENTS; DERIVATIVES; Decarboxylation coupling
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.202402716

Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible‐light‐induced decarboxylation coupling reaction between N‐hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy)3 as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product‐dithiocarbamates in high yields. This redox‐neutral protocol uses inexpensive and readily available starting material under mild reaction conditions, exhibiting broad substrate scope and wide functional group compatibility. This method can be further used for post modification of complex natural products and bioactive drugs. A new visible‐light‐induced decarboxylation coupling reaction between N‐hydroxyphthalimide esters and tetraalkylthiuram disulfides was reported. This redox‐neutral protocol uses inexpensive and readily available starting material under mild reaction conditions, exhibiting broad substrate scope and wide functional group compatibility. This method can be further used for post modification of complex natural products and bioactive drugs.