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

ABSTRACT: Summary B(C6F5)3·H2O has been long recognized as a common Brønsted acid. The lack of X-ray crystal structure of B(C6F5)3·H2O with other substrates has greatly limited the development of a new catalytic mode. In this work, a complex of B(C6F5)3·H2O 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(C6F5)3·H2O, 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. Graphical abstract Highlights • Aerobic oxidation under visible light conditions• No need for an external photocatalyst• Hydrogen bonds and π-π interactions between B(C6F5)3·H2O and amides were identified Organic reaction; Physical organic chemistry; Chemical phenomena

SUBMITTER: Wang S

PROVIDER: S-EPMC10148046 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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