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Synfacts 2025; 21(01): 34
DOI: 10.1055/a-2467-6217
Metals in Synthesis

Synthesis of 1-Indanones by Photoredox-Catalyzed (3+2) Annulation of Aromatic Amides with Olefins

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Dáiríne M. Morgan 
Tang Z, Yao Z, Yu Y, Huang J, Ma X, Zhao X, Chang Z, Zhao D *. Sun Yat-Sen University, Guangzhou, P. R. China
Photoredox-Catalyzed [3+2] Annulation of Aromatic Amides with Olefins via Iminium Intermediates.

Angew. Chem. Int. Ed. 2024;
DOI: 10.1002/anie.202412152
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Keywords

(3+2) annulation - aromatic amides - 1-indanones - olefins - photoredox catalysis

Significance

A photoredox-catalyzed (3 + 2) annulation of tertiary aromatic amides with olefins to form 1-indanones as well as enamines and amines is reported. This methodology makes use of an in situ generated electrophilic oxyiminium salt to overcome the low electrophilicity of amides.


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Comment

Radical trapping and radical cascade experiments were performed to support the proposed mechanism. The synthetic utility of the reaction was further demonstrated through derivatization of the product and a gram-scale reaction.


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Publication History

Article published online:
20 December 2024

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