4.8 Article

Stereoselective Pincer-Complex Catalyzed C-H Functionalization of Benzyl Nitriles under Mild Conditions. An Efficient Route to β-Aminonitriles

Journal

ORGANIC LETTERS
Volume 10, Issue 22, Pages 5175-5178

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol8021512

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Funding

  1. Swedish Research Council
  2. Erasmus Scholarship of the EU
  3. UPLC
  4. Alice and Knut Wallenberg Foundation

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An efficient palladium pincer-complex catalyzed reaction has been developed for (x-C-H bond functionalization of benzyl nitriles. The studied coupling reaction with sulfonylimines affords beta-aminonitriles with usually high levels of stereoselectivity. The stereoselectivity of the process is highly dependent on the electronic effects of the ortho substituents of the benzyl moiety. Promising levels of enantiomeric excess are obtained using chiral pincer complexes as catalysts.

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