Gatarz Sandra E, Griffiths Oliver M, Esteves Henrique A, Jiao Wenhua, Morse Peter, Fisher Ethan L, Blakemore David C, Ley Steven V
Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.
Medicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States.
J Org Chem. 2024 Feb 2;89(3):1898-1909. doi: 10.1021/acs.joc.3c02557. Epub 2024 Jan 18.
A method to assemble (hetero)aryl sulfonamides via the reductive coupling of aryl sulfinates and nitroarenes is reported. Various reducing conditions with sodium bisulfite and with or without tin(II) chloride in DMSO were developed using an ultrasound bath to improve reaction homogeneity and mixing. A range of (hetero)aryl sulfonamides bearing a selection of functional groups were prepared, and the mechanism of the transformation was investigated. These investigations have led us to propose the formation of nitrosoarene intermediates, which were established via an independent molecular coupling strategy.
报道了一种通过芳基亚磺酸盐与硝基芳烃的还原偶联来组装（杂）芳基磺酰胺的方法。使用超声浴开发了在二甲基亚砜中用亚硫酸氢钠以及有或没有氯化亚锡的各种还原条件，以提高反应均匀性和混合效果。制备了一系列带有多种官能团的（杂）芳基磺酰胺，并对转化机理进行了研究。这些研究使我们提出了亚硝基芳烃中间体的形成，该中间体是通过独立的分子偶联策略确定的。
