SCHEDULED MAINTENANCE
Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations†
*ab
Abstract
Despite indisputable progress in the development of electrochemical transformations, electrocatalytic annulations for the synthesis of biologically relevant three-dimensional spirocyclic compounds has as of yet not been accomplished. In sharp contrast, herein, we describe the palladaelectro-catalyzed C–H activation/[3 + 2] spiroannulation of alkynes by 1-aryl-2-naphthols. Likewise, a cationic rhodium(III) catalyst was shown to enable electrooxidative [3 + 2] spiroannulations via formal C(sp3)–H activations. The versatile spiroannulations featured a broad substrate scope, employing electricity as a green oxidant in lieu of stoichiometric chemical oxidants under mild conditions. An array of spirocyclic enones and diverse spiropyrazolones, bearing all-carbon quaternary stereogenic centers were thereby accessed in a user-friendly undivided cell setup, with molecular hydrogen as the sole byproduct.
![Graphical abstract: Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D1SC07124F&imageInfo.ImageIdentifier.Year=2022)
- This article is part of the themed collection: Most popular 2022 organic chemistry articles
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