Abstract
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.
Original language | English (US) |
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Pages (from-to) | 12217-12220 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 136 |
Issue number | 35 |
DOIs | |
State | Published - Sep 3 2014 |
All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry