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Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

Journal 2023 · IF 5.8 · 发表于 2023 年 3 月 30 日
作者: Shi-Jun Wang,Long Wang,Xiang-Ying Tang
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摘要

B(C 6 F 5 ) 3 ·H 2 O has been long recognized as a common Brønsted acid. The lack of X-ray crystal structure of B(C 6 F 5 ) 3 ·H 2 O with other substrates has greatly limited the development of a new catalytic mode. In this work, a complex of B(C 6 F 5 ) 3 ·H 2 O and amide 2-phenyl-3,4-dihydroisoquinolin-1( 2H )-one with hydrogen bonds and π-π interactions is characterized by X-ray diffraction. Such noncovalent interactions in solution also exist, as verified by NMR, UV-Vis absorption, and fluorescence emission measurements. Moreover, the mixture of amide 2-phenyl-3,4-dihydroisoquinolin-1( 2H )-one and B(C 6 F 5 ) 3 ·H 2 O, instead of other tested Brønsted acids, shows a tailing absorption band in the visible light region (400–450 nm). Based on the photoactive properties of the complex, a photoredox catalysis is developed to construct α -aminoamides under mild conditions.