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- W3203436587 abstract "Abstract The selective α‐deuteration of α,β‐unsaturated nitriles using the strong base t BuOK or a metal‐ligand cooperative Ru pincer catalyst is described. With D 2 O as deuterium source and glyme as solvent at 70 °C, t BuOK is an efficient catalyst for deuteration at the α‐C( sp 2 ) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the t BuOK‐catalysed protocol does not tolerate base‐sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein's ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal‐ligand cooperative Ru catalyst is found to be significantly higher than that of t BuOK, allowing reactions to proceed well even at room temperature. A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α‐CH position when using t BuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa‐Michael addition of D 2 O. magnified image" @default.
- W3203436587 created "2021-10-11" @default.
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- W3203436587 date "2021-10-08" @default.
- W3203436587 modified "2023-10-17" @default.
- W3203436587 title "Selective α‐Deuteration of Cinnamonitriles using D <sub>2</sub> O as Deuterium Source" @default.
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- W3203436587 doi "https://doi.org/10.1002/adsc.202101093" @default.
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