98446-82-3Relevant academic research and scientific papers
Iron Hydride Radical Reductive Alkylation of Unactivated Alkenes
Saladrigas, Mar,Bonjoch, Josep,Bradshaw, Ben
, p. 684 - 688 (2020/01/31)
Iron-catalyzed hydrogen atom transfer-mediated intermolecular C-C coupling reactions between alkenes and tosylhydrazones, followed by in situ cleavage of the tosylhydrazine intermediates using Et3N, are described. The process involves a new strategic bond disconnection resulting in the reductive alkylation of nonactivated alkenes. The reaction is operationally simple, proceeds under mild conditions, and has a wide substrate scope.
Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
, p. 3813 - 3818 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides
Huo, Shouquan
, p. 423 - 425 (2007/10/03)
(Matrix presented) Alkylzinc bromides have been efficiently prepared by the direct insertion of zinc metal (dust, powder, granule, shot), activated with 1-5 mol % I2, into alkyl bromides in a polar aprotic solvent. The zinc reagents thus formed undergo Ni- and Pd-catalyzed cross-coupling with aryl halides to produce functionalized alkylarenes in excellent yields.
THE EFFECT OF ARYL SUBSTITUENTS ON ARYLCARBENE REACTIVITY
Tomioka, Hideo,Tabayashi, Kazuo,Ozaki, Yasuji,Izawa, Yasuji
, p. 1435 - 1440 (2007/10/02)
Substituted (p-MeO, p-Me, H, p-Cl, p-Br, m-Br, m-MeO, 3,4-Cl2, p-CO2Me, m-CN and p-CN) monophenylcarbenes are generated in a binary mixture of substrates (methanol, cis-4-methyl-2-pentene and cyclohexane) and the relative rate of O - H insertion into methanol to stereospecific cyclopropanation of the olefin to C - H insertion into cyclohexane are calculated from the ratios of products and substrates.It is found (i) that the reactivities of the substrates decrease in the order of methanol, olefin and cyclohexane and (ii) that electron-donating substituents generally lead to reaction with the more reactive substrates while the reaction with the less reactive substrates is favoured in the case of electron-withdrawing substituents.These results are interpreted in terms of the change in the electrophilicity of the singlet arylcarbene by the substituents rather than the change in the singlet-triplet equilibrium.
