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Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers.

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We report herein that copper(I) catalysis using a bis(phosphine) dioxide ligand can catalyze the desymmetric C-H arylation of prochiral bipyrroles. More than 50 nitrogen-nitrogen atropisomers were achieved in good to… Click to show full abstract

We report herein that copper(I) catalysis using a bis(phosphine) dioxide ligand can catalyze the desymmetric C-H arylation of prochiral bipyrroles. More than 50 nitrogen-nitrogen atropisomers were achieved in good to excellent yields with excellent enantioselectivities (≤97% yield, ≤98% ee). The reaction proceeds under mild conditions with good functional group compatibility on arenes and diaryliodonium salts. Moreover, this principle enables iterative arylation of the bipyrroles to enantioselectively arylate different positions during the catalysis of copper.

Keywords: arylation; asymmetric arylation; pyrroles diaryliodonium; catalyzed asymmetric; diaryliodonium salts; arylation pyrroles

Journal Title: Organic letters
Year Published: 2022

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