Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, Campinas, São Paulo 13083-862, Brazil.
Institute of Chemistry of São Carlos, University of São Paulo, Avenida Trabalhador São-Carlense 400, São Carlos, São Paulo 13566-590, Brazil.
Org Lett. 2021 Dec 3;23(23):9292-9296. doi: 10.1021/acs.orglett.1c03662. Epub 2021 Nov 19.
Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3-trisubstituted β-lactams. The second approach describes the reaction with sulfoxides to afford the corresponding sulfoxonium ylides, followed by reaction with aryldiazoketones to produce 5-alkoxy-2,2,4-trisubstituted furan-3(2H)-ones. These protocols take advantage of the photolysis of aryldiazoacetates and the photochemically promoted Wolff rearrangement of aryldiazoketones.
介绍了两种新的可见光介导策略，起始原料为芳基重氮乙酸酯。第一种方法描述了它们与叠氮化物的反应，生成相应的亚胺，然后与芳基二氮烯酮反应，生成烷基 2-羧酸酯-2,3,3-三取代的β-内酰胺。第二种方法描述了与亚砜的反应，生成相应的亚磺酰基叶立德，然后与芳基二氮烯酮反应，生成 5-烷氧基-2,2,4-三取代的呋喃-3(2H)-酮。这些方案利用了芳基重氮乙酸酯的光解和芳基二氮烯酮的光化学促进的Wolff 重排。
