title: Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp(3))-H bonds.
abstract: Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp(3) )H and C(sp(2) )H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-CH methylation or γ-CH arylation step, the γ-C(sp(3) )H amination provided access to complex pyrrolidones from readily available precursors.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA).
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: William A
authors.initials: WA
authors.lastname: Nack
authors.forename: Qiong
authors.initials: Q
authors.lastname: Li
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000586:Amination; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011760:Pyrrolidinones; D010165:Palladium
keywords: CH amination; auxiliary groups; palladium; pyrrolidones; γ-lactams