title: Catalytic C6 functionalization of 2,3-disubstituted indoles by scandium triflate.
abstract: We report herein an unprecedented direct catalytic C6 functionalization reaction of 2,3-disubstituted indoles with various N-Ts aziridines catalyzed by Sc(OTf)3 under mild conditions. Mechanistic studies revealed that a kinetically favored but reversible formal [3 + 2] annulation occurs initially. The direct C6 functionalization, although having a relatively higher energetic barrier, delivers the thermodynamically favorable products.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, People's Republic of China.
authors.forename: Hua
authors.initials: H
authors.lastname: Liu
authors.forename: Chao
authors.initials: C
authors.lastname: Zheng
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D001388:Aziridines; D007211:Indoles; D008698:Mesylates; C436603:scandium triflate; D012538:Scandium