Issue 9, 2022

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 des. 2021
Accepted
09 feb. 2022
First published
10 feb. 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 2783-2788

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations

W. Wei, A. Scheremetjew and L. Ackermann, Chem. Sci., 2022, 13, 2783 DOI: 10.1039/D1SC07124F

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