Abstract
N-Methyl-N-((trimethylsilyl)methyl)aniline was employed as reagent in visible-light-induced, iridium-catalyzed addition reactions to cyclic α,β-unsaturated carbonyl compounds. Typical reaction conditions included the use of one equivalent of the reaction substrate, 1.5 equivalents of the aniline and 2.5 mol % (in MeOH) or 1.0 mol % (in CH2Cl2) [Ir(ppy)2(dtbbpy)]BF4 as the catalyst. Two major reaction products were obtained in combined yields of 3067%. One product resulted from aminomethyl radical addition, the other product was a tricyclic compound, which is likely formed by attack of the intermediately formed α-carbonyl radical at the phenyl ring. For five-membered α,β-unsaturated lactone and lactam substrates, the latter products were the only products isolated. For the six-membered lactones and lactams and for cyclopentenone the simple addition products prevailed.
Original language | English |
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Pages (from-to) | 890-896 |
Number of pages | 7 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 10 |
DOIs | |
State | Published - 17 Apr 2014 |
Keywords
- Cyclization
- Electron transfer
- Iridium
- Photochemistry
- Photoredox catalysis
- Radical reactions