Distinctive Reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under Photoredox Catalysis

Submitting author affiliation:
Chung-Ang University, Seoul, Korea, Republic of

Beilstein Arch. 2020, 202035. https://doi.org/10.3762/bxiv.2020.35.v1

Published 30 Mar 2020

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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 phenyl substituent in the aniline moiety of the substrate was critical for the reactivity. The reaction proceeded via radical-radical cross-coupling of a-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 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. 

Keywords: photocatalysis; imine; 1,2-diamine; visible light; diversity

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Tambe, S.; Min, K. H.; Iqbal, N.; Cho, E. J. Beilstein Arch. 2020, 202035. doi:10.3762/bxiv.2020.35.v1

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