title: Palladium-catalyzed unactivated C(sp3)-H bond activation and intramolecular amination of carboxamides: a new approach to β-lactams.
abstract: An efficient method to synthesize the β-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring β-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived β-lactams. This method has been applied to the efficient synthesis of the β-lactamase inhibitor MK-8712.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Wen-Wu
authors.initials: WW
authors.lastname: Sun
authors.forename: Pei
authors.initials: P
authors.lastname: Cao
authors.forename: Ren-Qiang
authors.initials: RQ
authors.lastname: Mei
authors.forename: Yue
authors.initials: Y
authors.lastname: Li
authors.forename: Yuan-Liang
authors.initials: YL
authors.lastname: Ma
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
mesh_terms: D000577:Amides / Q000737:chemistry*; D000586:Amination; D000634:Aminoquinolines / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D008997:Monobactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D065093:beta-Lactamase Inhibitors; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D000634:Aminoquinolines; C561926:MK 8712; D008997:Monobactams; D065093:beta-Lactamase Inhibitors; D047090:beta-Lactams; D010165:Palladium