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Light-Driven Deracemization of Benzylic Nitriles

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Light-Driven Deracemization of Benzylic Nitriles

🎊 We’re excited to highlight the latest work from Y. Emily Du and colleagues from the Robert Knowles Lab, recently published in JACS: 📄 “Multiplicative Stereocontrol in the Light-Driven Deracemization of Benzylic Nitriles” 🔖 https://lnkd.in/gX-REnFE This study reports a light-driven deracemization of benzylic nitriles enabled by cooperative photoredox and chiral phosphate catalysis. The method achieves up to 99% yield and 98% ee by combining t

🎊 We’re excited to highlight the latest work from Y. Emily Du and colleagues from the Robert Knowles Lab, recently published in JACS:

📄 “Multiplicative Stereocontrol in the Light-Driven Deracemization of Benzylic Nitriles”

🔖 https://lnkd.in/gX-REnFE

This study reports a light-driven deracemization of benzylic nitriles enabled by cooperative photoredox and chiral phosphate catalysis. The method achieves up to 99% yield and 98% ee by combining two moderately stereoselective steps: stereoablative oxidation and deprotonation, followed by stereoselective C–H bond formation to establish the α-nitrile stereocenter.

Competition between back electron transfer and deprotonation of a key arene radical cation intermediate results in selective processing of the minor enantiomer. The deprotonation step exhibits a primary kinetic isotope effect, while the stereoselectivity of the C–H bond-forming step correlates with the ground-state reduction potential of the photocatalyst. The participation of a single chiral catalyst in two cooperative stereoselective steps produces a non-classical nonlinear effect.

🧡 AmBeed in the Research

We’re honored to see that (S)-TRIP
CAS No. 874948-63-7 | Cat. No. A1324845, a chiral phosphoric acid catalyst used in this study, was sourced from us! 🧪✨

🐝 Exploring chiral phosphoric acid catalysts for your own research? Discover more AmBeed’s collection:
https://www.arctomsci.com

#ResearchUsingAmBeed #JACS #AsymmetricCatalysis #Deracemization #Stereocontrol #Photochemistry #OrganicChemistry #Catalysis

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Source: AmBeed LinkedIn post
LinkedIn publication date: 2026-10-03 (UTC, derived from the activity ID).

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