Organic Synthesis, Department of Chemistry , University of Antwerp , Groenenborgerlaan 171 , 2020 Antwerp , Belgium.
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS) , Vrije Universiteit Amsterdam , De Boelelaan 1108 , 1081 HZ Amsterdam , The Netherlands.
Org Lett. 2018 Jul 20;20(14):4235-4239. doi: 10.1021/acs.orglett.8b01654. Epub 2018 Jul 5.
The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation of challenging amides that are not or hardly accessible via classical approaches.
本文报道了从易得且稳定的取代 S-苯基硫代氨基甲酸酯和格氏试剂反应物合成仲酰胺的方法。氧化后处理可将硫负离子离去基团回收为二苯基二硫醚。二苯基二硫醚可转化为 S-苯基苯并硫代磺酸酯，这是合成硫代氨基甲酸酯所需的反应物。这种酰胺合成方法适用于制备具有挑战性的酰胺，这些酰胺通过经典方法难以或无法获得。
