Photocatalyzed Amination of Benzylic C(Sp3)−H Bonds Via C−N Coupling: Green Synthesis and Nmr Analysis of N-Benzylanilines

A facile, efficient and green photo-catalyzed amination of benzylic C(sp3)−H bonds via C−N coupling for the synthesis of novel N-benzylaniline derivatives starting from readily available toluene derivative and aniline derivative under irradiation of UV LEDs (365 nm) without using any bases, strong oxidants, complex ligands, or precious metals is reported. The N-benzylaniline products could be obtained under UV LEDs irradiation at room temperature in 12 h with definite compatibilities with functional groups. To discuss the characteristic pattern of armatic protons and carbons, to identify its structure, NMR spectra analysis (1D and 2D-NMR) was carried out in details by the chemical shifts, couplings and correlations. The energy levels of molecular orbitals (HOMO and LUMO) for N-benzylaniline product (3a) were investigated.

Keywords: Amination, C−N coupling, Green synthesis, NMR analysis, photocatalysis

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Tan, Hongbo and Lin, Chang-qiu and Ren, Si-ying and Peng, Yu-han and Zhang, Meng-qi and Xu, Zhi-gang and Tang, Dian-yong and Chen, Zhongzhu, Photocatalyzed Amination of Benzylic C(Sp3)−H Bonds Via C−N Coupling: Green Synthesis and Nmr Analysis of N-Benzylanilines. Available at SSRN: https://ssrn.com/abstract=4918746