Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5418-5422Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02328
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Funding
- National Natural Science Foundation of China [21602059, 21672059, 21561162003]
- China Postdoctoral Science Foundation [2016T90341]
- Eastern Scholar Distinguished Professor Program
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A novel copper-catalyzed radical cyanotrifluoromethylation has been achieved through a multicomponent reaction of isocyanides, Togni's reagent, and trimethylsilyl cyanides, affording trifluoroacetimidoyl nitriles in good yields. This reaction demonstrates a unique feature of merging two valuable functional groups trifluoromethyl (CF3) and cyan (CN)-onto the same C atom. The transformation proceeds by the initial addition of the CF3 radical to isocyanide and the subsequent intermolecular C-CN formation. The products can be successfully transformed to a series of CF3-containing amines and imines that may serve in the synthesis of valuable pharmaceuticals and agrochemicals.
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