What question did this study set out to answer?

To establish a redox-neutral, highly enantioselective α-coupling of N-arylaminomethanes with N-sulfonyl aldimines using dual catalytic activation.

October 11, 2015Journal of the American Chemical Society

Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines

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Authors

DUDaisuke UraguchiHokkaido University NKNatsuko KinoshitaUniversity of Tsukuba TKTomohito KizuJapan Science and Technology Agency

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Implication

Experimental study demonstrates redox-neutral enantioselective coupling of N-arylaminomethanes with aldimines using dual catalysis, highlighting a strategy to control radical bond formation.

Key Points

To establish a redox-neutral, highly enantioselective α-coupling of N-arylaminomethanes with N-sulfonyl aldimines using dual catalytic activation.
Combined a P-spiro chiral arylaminophosphonium barfate ionic Brønsted acid with a transition-metal photosensitizer.
Performed the coupling reactions under visible light irradiation to generate and guide reactive radical intermediates.
Achieved redox-neutral carbon-carbon bond formation yielding coupled products with high enantioselectivity.
Demonstrated catalytic control over stereoselective bond-forming pathways involving reactive radical species.

Cite This Study

Uraguchi et al. (2015) studied this question.

synapsesocial.com/papers/6a00dee74716aad0cc85dac4 https://doi.org/10.1021/jacs.5b09329

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Implication

Experimental study demonstrates redox-neutral enantioselective coupling of N-arylaminomethanes with aldimines using dual catalysis, highlighting a strategy to control radical bond formation.

Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines

Discussion

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Implication

Key Points

Cite This Study

Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines

Discussion

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Implication

Key Points

Cite This Study

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