Ligand-Enabled γ‑C(sp<sup>3</sup>)–H Olefination of Amines: En Route to Pyrrolidines

Abstract

Pd­(II)-catalyzed olefination of γ-C­(sp<sup>3</sup>)–H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C­(sp<sup>3</sup>)–H olefination reactions. The use of Ns protecting group to direct C­(sp<sup>3</sup>)–H activation of alkyl amines is also a significant step toward practical C–H functionalizations of alkyl amines

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