Regio- and stereoselective addition of allylmetal reagents to pyridinium-pi and quinolinium-pi complexes.
[reaction: see text] Regio- and stereoselective allylation of pyridinium and quinolinium salts was performed by the addition of allylindium and allyltributyltin reagents toward intermediary cation-pi complexes. The reaction with allylindium and allyltributyltin reagents afforded a 1,2-adduct, whereas the addition of a prenylindium reagent gave a 1,4-adduct with good regio- and stereoselectivities. X-ray structural analysis, 1H NMR studies, and DFT calculations elucidated the intermediary cation-pi complex formation with face-to-face orientation.
Yamada
Shinji
S
Department of Chemistry, Faculty of Science, Ochanomizu University, Bunkyo-ku, Tokyo 112-8610, Japan. yamada.shinji@ocha.ac.jp
Inoue
Mai
M
D002412:Cations / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry*; D011806:Quinolinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D002412:Cations; D008670:Metals; D011726:Pyridinium Compounds; D011806:Quinolinium Compounds