Journal
ORGANIC LETTERS
Volume 24, Issue 12, Pages 2271-2275Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00203
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Funding
- National Natural Science Foundation of China [21871171, 22171174]
- Natural Science Foundation of Shaanxi Province [2019JM-043]
- Fundamental Research Funds for the Central Universities [2020CBLY009]
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A light-promoted Ni-catalyzed cyanation reaction using 1,4-dicyanobenzene as a cyanating agent is described. Various aryl bromides, chlorides, and druglike molecules are converted to their corresponding nitriles (65 examples). Mechanistic studies reveal that under irradiation, the Ni(II)(dtbbpy)(p-C6H4CN)(CN) oxidative addition product undergoes homolytic cleavage of the Ni-aryl bond to generate an aryl radical and a Ni(I)-CN species, which initiates subsequent cyanation reactions.
A light-promoted Ni-catalyzed cyanation of aryl halides employing 1,4-dicyanobenzene as a cyanating agent is reported. A broad array of aryl bromides, chlorides, and druglike molecules could be converted into their corresponding nitriles (65 examples). Mechanistic studies suggest that upon irradiation, the oxidative addition product Ni(II)(dtbbpy)(p-C6H4CN)(CN) undergoes homolytic cleavage of the Ni-aryl bond to generate an aryl radical and a Ni(I)-CN species, the latter of which initiates subsequent cyanation reactions.
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