1266062-90-1Relevant articles and documents
Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation
Musacchio, Andrew J.,Nguyen, Lucas Q.,Beard, G. Hudson,Knowles, Robert R.
supporting information, p. 12217 - 12220 (2014/12/09)
While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.