66730-40-3Relevant academic research and scientific papers
Tandem Mn–I Exchange and Homocoupling Processes Mediated by a Synergistically Operative Lithium Manganate
Uzelac, Marina,Mastropierro, Pasquale,de Tullio, Marco,Borilovic, Ivana,Tarrés, Màrius,Kennedy, Alan R.,Aromí, Guillem,Hevia, Eva
supporting information, p. 3247 - 3253 (2020/12/11)
Pairing lithium and manganese(II) to form lithium manganate [Li2Mn(CH2SiMe3)4] enables the efficient direct Mn–I exchange of aryliodides, affording transient (aryl)lithium manganate intermediates which in turn undergo spontaneous C?C homocoupling at room temperature to furnish symmetrical (bis)aryls in good yields under mild reaction conditions. The combination of EPR with X-ray crystallographic studies has revealed the mixed Li/Mn constitution of the organometallic intermediates involved in these reactions, including the homocoupling step which had previously been thought to occur via a single-metal Mn aryl species. These studies show Li and Mn working together in a synergistic manner to facilitate both the Mn–I exchange and the C?C bond-forming steps. Both steps are carefully synchronized, with the concomitant generation of the alkyliodide ICH2SiMe3 during the Mn–I exchange being essential to the aryl homocoupling process, wherein it serves as an in situ generated oxidant.
Novel One-Pot Synthesis of 2-Pentafluoroethyl-3-trifluoromethyl-4H-quinolizin-4-ones and Related Compounds.
Konakahara, Takeo,Murayama, Takashi,Sano, Kazuya,Kubota, Shin
, p. 844 - 854 (2007/10/03)
A convenient novel method was developed to prepare 2-pentafluoroethyl-3-trifluoromethyl-4H-quinolizin-4-one 5a in 90percent yield by a one-pot reaction of 2-(trimethylsilylmethyl)pyridine 1a with perfluoro(2-methyl-2-pentene) 2 in the presence of potassium fluoride in tetrahydrofuran.The method was applied to the synthesis of the corresponding 6-methyl-, 8-methyl-, 1-methyl-, 6,8-dimethyl-, 6-ethyl-, 7-ethyl- and 7-aza-4H-quinolizin-4-one derivatives 5b - 5h and the corresponding 1H-pyridobenzothiazol-1-one derivative 7a and its benzoxazole analogue 7b in 89, 98, 21, 83, 70, 53, 32, 71 and 51percent yields, respectively.A reaction mechanism was also discussed on the basis of chemical transformation of both of the intermediates 3a and 4a into 5a.
