Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 11, Pages 7552-7562Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00592
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Funding
- SERB, India [CRG/2018/002480]
- IISER-Tirupati
- SwarnaJayanti Fellowship [DST/SJF/CSA-04/2019-2020, SERB/F/5892/2020-2021]
- SERB-PMRF, India
- UGC, India
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This study reports a nickel-catalyzed acceptorless dehydrogenative coupling reaction, which can access diverse substituted olefins. The method features a low-cost catalyst, good functional group compatibility, and high reaction selectivity and efficiency.
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.
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