Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditionsopen access
- Authors
- Tambe, Shrikant D.; Min, Kwan Hong; Iqbal, Naeem; Cho, Eun Jin
- Issue Date
- 18-Jun-2020
- Publisher
- BEILSTEIN-INSTITUT
- Keywords
- 1,2-diamine; diversity; imine; photocatalysis; visible light
- Citation
- BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, v.16, pp 1335 - 1342
- Pages
- 8
- Journal Title
- BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 16
- Start Page
- 1335
- End Page
- 1342
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/42108
- DOI
- 10.3762/bjoc.16.114
- ISSN
- 1860-5397
- Abstract
- A simple photocatalytic method was developed for the synthesis of unsymmetrical 1,2-diamines by the unprecedented reductive coupling of N-benzylidene-[1,1'-biphenyl]-2-amines with an aliphatic amine. The presence of a phenyl substituent in the aniline moiety of the substrate was critical for the reactivity. The reaction proceeded via radical-radical cross-coupling of alpha-amino radicals generated by proton-coupled single-electron transfer in the presence of an Ir photocatalyst. On the other hand, symmetrical 1,2-diamines were selectively produced from the same starting materials by the judicious choice of the reaction conditions, showcasing the distinct reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines. The developed method can be employed for the synthesis of various bulky vicinal diamines, which are potential ligands in stereoselective synthesis.
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