Regiodivergent Copper Catalyzed Borocyanation of 1,3‐Dienes

Copper catalyzed multi‐functionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequent...

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Veröffentlicht in:Angewandte Chemie International Edition 2018-08, Vol.57 (35), p.11305-11309
Hauptverfasser: Jia, Tao, He, Qiong, Ruscoe, Rebecca E., Pulis, Alexander P., Procter, David J.
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Sprache:eng
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Zusammenfassung:Copper catalyzed multi‐functionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2‐ or 4,3‐borocyanation products. A powerful tool for the generation of complex molecules is the copper catalyzed multi‐functionalization of unsaturated carbon‐carbon bonds. A regiodivergent process that allows a switch between 1,4‐ and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand is described.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201806169