106520-92-7Relevant academic research and scientific papers
Iron-copper cooperative catalysis in the reactions of alkyl grignard reagents: Exchange reaction with alkenes and carbometalation of alkynes
Shirakawa, Eiji,Ikeda, Daiji,Masui, Seiji,Yoshida, Masatoshi,Hayashi, Tamio
supporting information; experimental part, p. 272 - 279 (2012/03/07)
Iron-copper cooperative catalysis is shown to be effective for an alkene-Grignard exchange reaction and alkylmagnesiation of alkynes. The Grignard exchange between terminal alkenes (RCH=CH2) and cyclopentylmagnesium bromide was catalyzed by FeCl3 (2.5 mol %) and CuBr (5 mol %) in combination with PBu3 (10 mol %) to give RCH2CH 2MgBr in high yields. 1-Alkyl Grignard reagents add to alkynes in the presence of a catalyst system consisting of Fe(acac)3, CuBr, PBu3, and N,N,N″,N″-tetramethylethylenediamine to give β-alkylvinyl Grignard reagents. The exchange reaction and carbometalation take place on iron, whereas copper assists with the exchange of organic groups between organoiron and organomagnesium species through transmetalation with these species. Sequential reactions consisting of the alkene-Grignard exchange and the alkylmagnesiation of alkynes were successfully conducted by adding an alkyne to a mixture of the first reaction. Isomerization of Grignard reagents from 2-alkyl to 1-alkyl catalyzed by Fe-Cu also is applicable as the first 1-alkyl Grignard formation step.
Iron-catalyzed carbolithiation of alkynes having no heteroatoms
Shirakawa, Eiji,Ikeda, Daiji,Ozawa, Tsubasa,Watanabe, Shogo,Hayashi, Tamio
supporting information; experimental part, p. 1885 - 1887 (2009/10/17)
Alkyl- and aryllithium compounds were found to add to alkynes having no heteroatoms in the presence of an iron or iron-copper catalyst to give various trisubstituted vinyllithium compounds.
Manganese-catalyzed cross-coupling reaction between aryl grignard reagents and alkenyl halides
Cahiez, Gerard,Gager, Olivier,Lecomte, Fabien
supporting information; experimental part, p. 5255 - 5256 (2009/05/30)
(Chemical Equation Presented) Aryl Grignard reagents react stereospecifically with alkenyl halides in the presence of manganese chloride (10%) to afford good yields of cross-coupling products.
ORGANIC SYNTHESIS USING HALOBORATION REACTIONS 11. A FORMAL CARBOBORATION REACTION OF 1-ALKYNES AND ITS APPLICATION TO THE DI- AND TRISUBSTITUTED ALKENE SYNTHESIS
Satoh, Yoshitaka,Serizawa, Hirokazu,Miyaura, Norio,Hara, Shoji,Suzuki, Akira
, p. 1811 - 1814 (2007/10/02)
The cross-coupling reaction of organozinc chlorides with (Z)-2-bromo-1-alkenylboranes prepared by the bromoboration reaction of 1-alkynes with tribromoborane, proceeds in the presence of a palladium catalyst to give 2,2-disubstituted alkenylboranes, which can be used for the di- or trisubstituted alkene synthesis directly.
