title: Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: a versatile access to furoquinoline and pyranoquinoline cores.
abstract: An efficient and versatile tandem process of acetalization and cycloisomerization reactions has been developed for the reactions of 1-alkynyl-2-carbonylquinoline substrates. The reaction occurs thanks to Au(I) and Ag(I) catalysis. Silver(I) catalysis has been extensively studied (11 different silver species) on a broad range of quinoline derivatives (variation of alkyne substituent, of carbonyl function and of nucleophiles), leading to a variety of furoquinoline and pyranoquinoline moieties. An insight is given for the presumed mechanism along with DFT-B3 LYP/6-31G** calculations to address the 6-endo and 5-exo regioselectivities observed.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, Université Claude Bernard, Lyon I. UMR CNRS 5246, Bâtiment CPE, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Godet
authors.forename: Carine
authors.initials: C
authors.lastname: Vaxelaire
authors.forename: Carine
authors.initials: C
authors.lastname: Michel
authors.forename: Anne
authors.initials: A
authors.lastname: Milet
authors.forename: Philippe
authors.initials: P
authors.lastname: Belmont
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000480:Alkynes; D011714:Pyrans; D011804:Quinolines; D012834:Silver; D006046:Gold