title: Ru-catalysed C-H silylation of unprotected gramines, tryptamines and their congeners.
abstract: Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.
authors.affiliation: Department of Chemistry - BMC, Uppsala University, Box 576, 75-123, Uppsala, Sweden. lukasz.pilarski@kemi.uu.se.
authors.forename: K
authors.initials: K
authors.lastname: Devaraj
authors.forename: C
authors.initials: C
authors.lastname: Sollert
authors.forename: C
authors.initials: C
authors.lastname: Juds
authors.forename: P J
authors.initials: PJ
authors.lastname: Gates
authors.forename: L T
authors.initials: LT
authors.lastname: Pilarski
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D026121:Indole Alkaloids; D008956:Models, Chemical; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*; D014363:Tryptamines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D017646:Organosilicon Compounds; D014363:Tryptamines; D012428:Ruthenium; C007884:gramine