Tandem Acceptorless Dehydrogenative Coupling–Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by...

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Veröffentlicht in:Journal of organic chemistry 2021-06, Vol.86 (11), p.7552-7562
Hauptverfasser: Midya, Siba P, Subaramanian, Murugan, Babu, Reshma, Yadav, Vinita, Balaraman, Ekambaram
Format: Artikel
Sprache:eng
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Zusammenfassung:The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented CC bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00592