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

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-catalyze...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2022-03, Vol.13 (9), p.2783-2788
Main Authors: Wei, Wen, Scheremetjew, Alexej, Ackermann, Lutz
Format: Article
Language:English
Subjects:
Alkynes
Catalysis
Chemistry
Clean energy
Enantiomers
Oxidizing agents
Palladium
Rhodium
Substrates
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Summary: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(sp 3 )-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. 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.
ISSN:2041-6520
2041-6539
DOI:10.1039/d1sc07124f