Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai, 201620, China.
Angew Chem Int Ed Engl. 2022 Mar 14;61(12):e202115687. doi: 10.1002/anie.202115687. Epub 2022 Feb 3.
The first C-SCF /SeCF cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF or Me NSeCF , 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.
首次报道了使用金氧化还原催化 [(MeDalphos)AuCl]、AgSCF 或 Me 3NSeCF 以及卤代烃作为底物的第一例 C-SCF/SeCF 交叉偶联反应。该新方法可实现芳基/烯基/炔基三氟甲基硫代和硒醚的一站式合成,具有广泛的底物范围 (>60 个实例,分离收率高达 97%)。该方法具有可扩展性,通过对各种生物活性分子的后期官能化证明了其稳健性,这使得该反应成为药物和农用化学品研发中合成三氟甲基硫代和硒醚的一种有吸引力的替代方法。