title: Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: application to the total synthesis of (±)-rhazinilam.
abstract: A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.
authors.affiliation: State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Youla
authors.initials: Y
authors.lastname: Su
authors.forename: Haipin
authors.initials: H
authors.lastname: Zhou
authors.forename: Jiaxuan
authors.initials: J
authors.lastname: Chen
authors.forename: Jinyi
authors.initials: J
authors.lastname: Xu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Wu
authors.forename: Aijun
authors.initials: A
authors.lastname: Lin
authors.forename: Hequan
authors.initials: H
authors.lastname: Yao
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D002264:Carboxylic Acids; D007212:Indolizines; D007769:Lactams; D011758:Pyrroles; D012997:Solvents; C009170:rhazinilam; D010165:Palladium