Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: a versatile access to furoquinoline and pyranoquinoline cores.
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.
Godet
Thomas
T
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.
Vaxelaire
Carine
C
Michel
Carine
C
Milet
Anne
A
Belmont
Philippe
P
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
D000480:Alkynes; D011714:Pyrans; D011804:Quinolines; D012834:Silver; D006046:Gold