title: C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.
abstract: A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation-C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue 18-292, Cambridge, Massachusetts 02139, United States.
authors.forename: Richard P
authors.initials: RP
authors.lastname: Loach
authors.forename: Owen S
authors.initials: OS
authors.lastname: Fenton
authors.forename: Kazuma
authors.initials: K
authors.lastname: Amaike
authors.forename: Dustin S
authors.initials: DS
authors.lastname: Siegel
authors.forename: Erhan
authors.initials: E
authors.lastname: Ozkal
authors.forename: Mohammad
authors.initials: M
authors.lastname: Movassaghi
mesh_terms: D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D014363:Tryptamines / Q000737:chemistry*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D014363:Tryptamines; D007495:Iridium; D010165:Palladium; D014364:Tryptophan