期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 145, 期 40, 页码 21738-21744出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.3c08428
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We report a light-driven method for the intermolecular anti-Markovnikov hydroamination of alkenes with primary heteroaryl amines. This method exhibits broad functional group tolerance and good reactivity. The reported method has important application value for pharmaceutically relevant heteroaryl amines.
We report a light-driven method for the intermolecular anti-Markovnikov hydroamination of alkenes with primary heteroaryl amines. In this protocol, electron transfer between an amine substrate and an excited-state iridium photocatalyst affords an aminium radical cation (ARC) intermediate that undergoes C-N bond formation with a nucleophilic alkene. Integral to reaction success is the electronic character of the amine, wherein increasingly electron-deficient heteroaryl amines generate increasingly reactive ARCs. Counteranion-dependent reactivity is observed, and iridium triflate photocatalysts are employed in place of conventional iridium hexafluorophosphate complexes. This method exhibits broad functional group tolerance across 55 examples of N-alkylated products derived from pharmaceutically relevant heteroaryl amines.
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