title: Platinum-catalyzed domino reaction with benziodoxole reagents for accessing benzene-alkynylated indoles.
abstract: Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrrole ring. To access benzene-ring-functionalized indoles with an unsubstituted pyrrole ring remains more challenging. Reported herein is a platinum-catalyzed cyclization/alkynylation domino process to selectively obtain C5- or C6-functionalized indoles starting from easily available pyrroles. The work combines, for the first time, a platinum catalyst with ethynylbenziodoxole hypervalent iodine reagents in a domino process for the synthesis of polyfunctionalized arene rings and gives access to important building blocks for the synthesis of bioactive compounds and organic materials.
authors.affiliation: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
authors.forename: Yifan
authors.initials: Y
authors.lastname: Li
authors.forename: Jerome
authors.initials: J
authors.lastname: Waser
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*
chemical_list: D000480:Alkynes; D007211:Indoles; D007462:Iodobenzenes; D007463:Iodobenzoates; C476101:o-iodoxybenzoic acid; D010984:Platinum
keywords: alkynes; cyclization; heterocycles; hypervalent compounds; platinum