title: Exploiting Aryl Mesylates and Tosylates in Catalytic Mono-α-arylation of Aryl- and Heteroarylketones.
abstract: The first general palladium catalyst for the catalytic mono-α-arylation of aryl- and heteroarylketones with aryl mesylates and tosylates is described. The newly developed indolyl-derived phosphine ligand L7 has been identified to promote this reaction efficiently. The key to success is attributed to the enhanced steric congestion of the catalyst and effective oxidative addition of the C(Ar)-OMs bond. In the presence of Pd(OAc)2 (0.25-2.5 mol %) and L7, selective monoarylations are achieved with ample reaction scope and product yields up to 95%. Importantly, we demonstrated the applicability of this protocol with the modification of biological phenolic compounds, rendering it amenable for functionalization of phenolic (pro)drugs.
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University , Hung Hom, Kowloon, Hong Kong.
authors.forename: Wai Chung
authors.initials: WC
authors.lastname: Fu
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University , Hung Hom, Kowloon, Hong Kong.
authors.forename: Chau Ming
authors.initials: CM
authors.lastname: So
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University , Hung Hom, Kowloon, Hong Kong.
authors.forename: On Ying
authors.initials: OY
authors.lastname: Yuen
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University , Hung Hom, Kowloon, Hong Kong.
authors.forename: Irene Toi Chuk
authors.initials: IT
authors.lastname: Lee
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University , Hung Hom, Kowloon, Hong Kong.
authors.forename: Fuk Yee
authors.initials: FY
authors.lastname: Kwong
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007659:Ketones; D008698:Mesylates; D010720:Phosphines; D014105:Tosyl Compounds; D010165:Palladium; C044646:phosphine