title: Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.
abstract: Pd(II)-catalyzed olefination of γ-C(sp(3))-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(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Heng
authors.initials: H
authors.lastname: Jiang
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jian
authors.initials: J
authors.lastname: He
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Tao
authors.initials: T
authors.lastname: Liu
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry; D008024:Ligands; D010165:Palladium / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000588:Amines; D002614:Chelating Agents; D005296:Ferrous Compounds; D008024:Ligands; D011759:Pyrrolidines; D010165:Palladium