Work

Gold (I/III)‐Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

Year: 2022

Type: article

Abstract: The first C−SCF3/SeCF3cross‐coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one‐stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio‐ and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late‐stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio‐ and selenoethers for pharmaceutical and agrochemical research and development.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202115687

Authors: Sagar R. Mudshinge, Yuhao Yang, Bo Xu, Gerald B. Hammond, Zhichao Lu

Institutions: University of Louisville, Donghua University

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry

Awards: Roles of Contact Ion-Pairs as Promoters or Catalysts in Organic Reactions, G1887947200, G2075426237, Nucleophilic halogenation reagents