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Intramolecular Azo Coupling Reaction of Binaphthyl Compounds: Synthesis of Pyrazole-Containing Helicene-Like Molecules.

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A method for accessing pyrazole-containing helicene-like molecules from easily accessible NOBIN derivatives was developed. The reaction proceeded efficiently via diazonium salt intermediates, which provided a series of helicene-like molecular products… Click to show full abstract

A method for accessing pyrazole-containing helicene-like molecules from easily accessible NOBIN derivatives was developed. The reaction proceeded efficiently via diazonium salt intermediates, which provided a series of helicene-like molecular products in yields of 77%-89% regardless of their steric and electronic natures. The photophysical properties of the products were investigated. The 3,3'-disubstituted molecules showed a characteristic blue shift in their emission spectra. Product derivatizations were conducted, and interesting reactivities toward nucleophiles were observed.

Keywords: containing helicene; reaction; helicene like; helicene; like molecules; pyrazole containing

Journal Title: Organic letters
Year Published: 2023

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