title: Organocatalytic arylation of 3-indolylmethanols via chemo- and regiospecific C6-functionalization of indoles.
abstract: An organocatalytic arylation of 3-indolylmethanols has been established via chemo- and regiospecific C6-functionalization of 2,3-disubstituted indoles, leading to the production of bisindolyloxindoles containing an all-carbon quaternary stereocenter in high yields (up to 99% yield). This reaction not only represents the first catalytic arylation of 3-indolylmethanols using 2,3-disubstituted indoles as aromatic nucleophiles but also serves as a good example of direct catalytic C6-functionalization of indoles, which have been scarcely investigated. Besides, this approach also provides an efficient method to access a biologically important 3,3'-disubstituted oxindole framework and a 3',6-linked bisindole skeleton. Furthermore, the investigation of the activation mode suggested that the dual activation of an ion pair and H-bond between the substrates and the catalyst cooperatively contributed to the success of the reaction.
authors.affiliation: School of Chemistry & Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, 221116, China.
authors.forename: Lu-Jia
authors.initials: LJ
authors.lastname: Zhou
authors.forename: Yu-Chen
authors.initials: YC
authors.lastname: Zhang
authors.forename: Jia-Jia
authors.initials: JJ
authors.lastname: Zhao
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
mesh_terms: D002384:Catalysis; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D007477:Ions; D000078183:Oxindoles; C022960:2-oxindole; D010165:Palladium