title: Hg(OTf)(2)-catalyzed direct vinylation of tryptamines and versatile applications for tandem reactions.
abstract: We have developed a unique catalytic protocol for direct gem-vinylation of tryptamine derivatives employing Hg(OTf)(2) as the optimum catalyst. The intermolecular vinylations with a series of aromatic acetylenes proceeded under ambient temperature at the C2 positions of indoles with high functional group tolerance. Based on the mechanistic insights, we further developed the tandem reactions successfully constructing a quaternary center.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, N10 W8, Sapporo 060-0810, Japan.
authors.forename: Haruki
authors.initials: H
authors.lastname: Mizoguchi
authors.forename: Hideaki
authors.initials: H
authors.lastname: Oikawa
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oguri
mesh_terms: D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature; D014363:Tryptamines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D007211:Indoles; D008698:Mesylates; D014363:Tryptamines; D014753:Vinyl Compounds; C012077:trifluoromethanesulfonic acid