title: Palladium-catalyzed Cs2CO3-promoted arylation of unactivated C(sp(3))-H bonds by (diacetoxyiodo)arenes: shifting the reactivity of (diacetoxyiodo)arenes from acetoxylation to arylation.
abstract: PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
authors.forename: Quan
authors.initials: Q
authors.lastname: Gou
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
authors.forename: Zhao-Fu
authors.initials: ZF
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
authors.forename: Zhi-Cheng
authors.initials: ZC
authors.lastname: Liu
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Qin
mesh_terms: D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002586:Cesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011619:Psychotropic Drugs / Q000138:chemical synthesis* / Q000737:chemistry; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002254:Carbonates; D009942:Organometallic Compounds; D011619:Psychotropic Drugs; D002586:Cesium; D005680:gamma-Aminobutyric Acid; D010165:Palladium; C545311:cesium carbonate; C008842:4-amino-3-phenylbutyric acid