Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α‑Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones
journal contributionposted on 08.04.2019, 18:33 by Xi Chen, Muhua Wang, Xinying Zhang, Xuesen Fan
An unprecedented cascade reaction of benzoyl sulfoxonium ylides with α-diazocarbonyl compounds leading to the formation of highly functionalized naphthalenones containing a β-ketosulfoxonium ylide moiety is presented. Promisingly, the naphthalenone derivative thus obtained was found to be a versatile intermediate toward diversely functionalized naphthalene derivatives including substituted 1-naphthol, 2-hydroxynaphthalen-1(2H)-one, naphthalen-1,2-dione, and 2-(methylsulfinyl)naphthalen-1-ol.
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α- diazocarbonyl compounds1- naphtholAccesscascade reactionbenzoyl sulfoxonium ylidesRhβ- ketosulfoxonium ylide moietyhydroxynaphthalendiversely functionalized naphthalene derivativesFunctionalized NaphthalenonesCompound2-PromisinglyCascadeformationmethylsulfinylfunctionalized naphthalenonesSulfoxonium YlidesDiazocarbonyl