title: Ligand Controlled Regiodivergent C1 Insertion on Arynes for Construction of Phenanthridinone and Acridone Alkaloids.
abstract: A palladium-catalyzed regiodivergent C1 insertion multicomponent reaction involving aryne, CO, and 2-iodoaniline is established to construct the scaffolds of phenanthridinone and acridone alkaloids. Regioselective control is achieved under the guidance of selective ligands. The phenanthridinones are solely obtained under ligand-free condition. In comparison, application of the electron-abundant bidentate ligand dppm afforded the acridones with high efficiency. The release rate of the aryne from the precursor assists the regioselectivity of insertion as well, which was revealed through interval NMR tracking. A plausible mechanism was suggested based on the control experiments. Representative natural products and two types of natural product analogues were synthesized divergently through this tunable method.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai, 200062 (P.R. China).
authors.forename: Minghao
authors.initials: M
authors.lastname: Feng
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai, 200062 (P.R. China).
authors.forename: Bingqing
authors.initials: B
authors.lastname: Tang
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai, 200062 (P.R. China).
authors.forename: Nengzhong
authors.initials: N
authors.lastname: Wang
authors.affiliation: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Cai Lun Lu 1200, Shanghai, 201203 (P.R. China).
authors.forename: Hong-Xi
authors.initials: HX
authors.lastname: Xu
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai, 200062 (P.R. China). xfjiang@chem.ecnu.edu.cn.|State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, (P.R. China). xfjiang@chem.ecnu.edu.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai (P.R. China). xfjiang@chem.ecnu.edu.cn.|School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Cai Lun Lu 1200, Shanghai, 201203 (P.R. China). xfjiang@chem.ecnu.edu.cn.
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Jiang
mesh_terms: D054831:Acridones / Q000138:chemical synthesis* / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D054831:Acridones; D000470:Alkaloids; D000480:Alkynes; D008024:Ligands; D010616:Phenanthrenes; D010165:Palladium; C040601:phenanthridone
keywords: acridones; arynes; ligand control; multicomponent reactions; phenanthridinones