Visible‐Light‐Mediated Dual Decarboxylative Coupling of Redox‐Active Esters with α,β‐Unsaturated Carboxylic Acids

An efficient visible‐light‐induced decarboxylative coupling between α,β‐unsaturated carboxylic acids and alkyl N‐hydroxyphthalimide esters has been developed. A wide range of redox‐active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) proved viable in this dual decarboxylation proces...

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Veröffentlicht in:Chemistry : a European journal 2017-08, Vol.23 (43), p.10259-10263
Hauptverfasser: Zhang, Jin‐Jiang, Yang, Jun‐Cheng, Guo, Li‐Na, Duan, Xin‐Hua
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Sprache:eng
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Zusammenfassung:An efficient visible‐light‐induced decarboxylative coupling between α,β‐unsaturated carboxylic acids and alkyl N‐hydroxyphthalimide esters has been developed. A wide range of redox‐active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) proved viable in this dual decarboxylation process, affording a broad scope of substituted alkenes in moderate to excellent yields with good E/Z selectivities. This redox‐neutral procedure was highlighted by its mild conditions, operational simplicity, easy accessibility of carboxylic acids, and excellent functional‐group tolerance. Light is the key: An efficient, redox‐neutral visible‐light‐induced decarboxylative coupling between α,β‐unsaturated carboxylic acids and alkyl N‐hydroxyphthalimide esters has been developed. This operationally simple sequential decarboxylation procedure afforded a broad scope of structurally diverse alkenes in moderate to excellent yields with good E/Z selectivities under mild conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201702200