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Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.

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 ?-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.

SUBMITTER: Tambe SD

PROVIDER: S-EPMC7308614 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Distinctive reactivity of <i>N</i>-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.

Tambe Shrikant D SD Min Kwan Hong KH Iqbal Naeem N Cho Eun Jin EJ

Beilstein journal of organic chemistry 20200618

A simple photocatalytic method was developed for the synthesis of unsymmetrical 1,2-diamines by the unprecedented reductive coupling of <i>N</i>-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 α-amino radicals generated by proton-coupled single-electron transfer in the presence of an Ir photocatalyst. On the other ...[more]

PMID: 32595781

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