Benzyl radical is added regioselectively to the carbonยฑnitrogen double bond of aromatic imines by UV irradiation (l>300 nm) of a ternary mixture of benzyl bromide/aromatic imines/1-benzyl-1,4-dihydronicotinamide (BNAH) in acetonitrile via a BNAH-mediated photoinduced electron transfer mechanism.
Radical addition to aromatic aldoximes
โ Scribed by Grossi, Loris; Lunazzi, Lodovico; Placucci, Giuseppe
- Book ID
- 120247316
- Publisher
- Royal Society of Chemistry
- Year
- 1983
- Tongue
- English
- Weight
- 579 KB
- Volume
- 9
- Category
- Article
- ISSN
- 1472-779X
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๐ SIMILAR VOLUMES
The first example of intermolecular carbon radical addition to unactivated aldoxime ethers in the preseace of BF3.OEt2 has provided a new efficient carbon-carbon bond-forming method for the synthesis of a variety of amines.
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New methodology for radical aromatic substitution has been developed involving the addition of electron-deficient radicals to unprotected pyrroles and indole. This non-oxidative process is presumed to be occurring via atom-transfer addition of suitable organoiodides and bromides with subsequent non-