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Synfacts 2024; 20(02): 0147
DOI: 10.1055/s-0043-1772987
Metals in Synthesis

Photoelectrocatalyzed Synthesis of Chiral Cyclobutanes

Contributor(s):
Mark Lautens
,
Alexa Torelli
Xiong P, Ivlev I, Meggers SE. * Philipps-Universität Marburg, Germany
Photoelectrochemical Asymmetric Dehydrogenative [2 + 2] Cycloaddition between C–C Single and Double Bonds via the Activation of Two C(sp3)–H Bonds.

Nat. Catal. 2023;
DOI: 10.1038/s41929-023-01050-y
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Key words

rhodium catalysis - photoelectrocatalysis - C–H bond activation

Significance

Meggers and co-workers describe an enantioselective [2 + 2] photocycloaddition between alkyl ketones and alkenes to synthesize cyclobutanes. The method utilizes electrocatalysis to activate two C(sp3 )–H bonds, and, under blue light irradiation, promotes coupling with two C(sp2) carbons. The procedure highlights a sustainable approach to asymmetric small ring synthesis.


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Comment

Alkyl tethered (hetero)aryl ketones and various aryl- and alkyl-substituted alkenes can react in a highly enantioselective fashion. The transformation can be performed on gram-scale. It is proposed that the role of ferrocene serves as a redox mediator to turn over the electrocatalytic system, while a chiral rhodium Lewis acid mediates the dehydrogenation of the ketone (I to VI) and the subsequent cycloaddition (VII to IX).


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Publication History

Article published online:
16 January 2024

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