Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 1, Pages 468-478Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b10870
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Funding
- Fellowship for Disruptive Chemistry at Merck & Co., Inc., Kenilworth, NJ, USA
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Accessing hindered amines, particularly primary amines alpha to a fully substituted carbon center, is synthetically challenging. We report an electrochemical method to access such hindered amines starting from benchtop-stable iminium salts and cyanoheteroarenes. A wide variety of substituted heterocycles (pyridine, pyrimidine, pyrazine, purine, azaindole) can be utilized in the cross-coupling reaction, including those substituted with a halide, trifluoromethyl, ester, amide, or ether group, a heterocycle, or an unprotected alcohol or alkyne. Mechanistic insight based on DFT data, as well as cyclic voltammetry and NMR spectroscopy, suggests that a proton-coupled electron-transfer mechanism is operational as part of a hetero-biradical cross-coupling of a-amino radicals and radicals derived from cyanoheteroarenes.
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