Selective Reductive Elimination at Alkyl Palladium(IV) by Dissociative Ligand Ionization: Catalytic C(sp3)−H Amination to Azetidines |
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| Authors: | Manuel Nappi Chuan He William G Whitehurst Ben G N Chappell Prof?Dr Matthew J Gaunt |
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| Institution: | Department of Chemistry, University of Cambridge, Cambridge, UK |
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| Abstract: | A palladium(II)‐catalyzed γ‐C?H amination of cyclic alkyl amines to deliver highly substituted azetidines is reported. The use of a benziodoxole tosylate oxidant in combination with AgOAc was found to be crucial for controlling a selective reductive elimination pathway to the azetidines. The process is tolerant of a range of functional groups, including structural features derived from chiral α‐amino alcohols, and leads to the diastereoselective formation of enantiopure azetidines. |
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| Keywords: | azetidines C− H activation hypervalent compounds palladium reaction mechanisms |
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