title: Gold-Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon.
abstract: A gold-catalyzed cascade annulation of propargylic silyl ethers with anthranils proceeds through a sequential ring opening/1,2-H-shift/protodeauration/Mukaiyama aldol cyclization. This method offers a regiospecific and modular access to 2-aminoquinolines and other quinoline derivatives under mild conditions and with a broad functional-group tolerance. The conversion is possible on a gram scale, which underlines the synthetic practicability of this methodology. The versatility of the obtained scaffold has been demonstrated by useful postfunctionalization.
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Hongming
authors.initials: H
authors.lastname: Jin
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Bin
authors.initials: B
authors.lastname: Tian
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Xinlong
authors.initials: X
authors.lastname: Song
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. xj850626@163.com.
authors.forename: Jin
authors.initials: J
authors.lastname: Xie
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Rudolph
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. hashmi@hashmi.de.|Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), 21589, Jeddah, Saudi Arabia. hashmi@hashmi.de.
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
keywords: alkynes; carbenes; gold catalysis; quinolines; umpolung