33206-73-4Relevant academic research and scientific papers
Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation
Basch, Corey H.,Liao, Jennie,Xu, Jianyu,Piane, Jacob J.,Watson, Mary P.
, p. 5313 - 5316 (2017/04/27)
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIII catalytic cycle.
Simplifying iron-phosphine catalysts for cross-coupling reactions
Bedford, Robin B.,Carter, Emma,Cogswell, Paul M.,Gower, Nicholas J.,Haddow, Mairi F.,Harvey, Jeremy N.,Murphy, Damien M.,Neeve, Emily C.,Nunn, Joshua
supporting information, p. 1285 - 1288 (2013/03/13)
Any old iron? Iron catalysts based on the widely available diphosphine ligand bis(diphenylphosphino)ethane have not previously fared particularly well in iron-catalyzed cross-coupling processes. However, this turns out not to be due to any inherently poor performance associated with the ligand, but rather the need to form a bis-chelate complex, either before or during the formation of an active FeI species. Copyright
Cross-coupling of non-activated chloroalkanes with aryl grignard reagents in the presence of iron/N-heterocyclic carbene catalysts
Ghorai, Sujit K.,Jin, Masayoshi,Hatakeyama, Takuji,Nakamura, Masaharu
supporting information; experimental part, p. 1066 - 1069 (2012/04/10)
An efficient and high-yielding cross-coupling reaction of various primary, secondary, and tertiary alkyl chlorides with aryl Grignard reagents was achieved by using catalytic amounts of N-heterocyclic carbene ligands and iron salts. This reaction is a simple and efficient arylation method having applicability to a wide range of industrially abundant chloroalkanes, including polychloroalkanes, which are challenging substrates under conventional cross-coupling conditions.
Iron(II) complexes with functionalized amine-pyrazolyl tripodal ligands in the cross-coupling of aryl Grignard with alkyl halides
Xue, Fei,Zhao, Jin,Hor, T. S. Andy
experimental part, p. 8935 - 8940 (2011/10/19)
Structurally distinctive Fe(ii) complexes with furan, thiophene and pyridine functionalized amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. The tether substituent at the central amine plays an active role in determining the coordination mode of the ligand and the metal geometry. All complexes are catalytically active towards cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides with β-hydrogen under ambient conditions. ESI-MS spectra analysis revealed the ligand-stabilised Fe(ii) and Mg(ii) species. The Royal Society of Chemistry 2011.
Air-stable secondary phosphine oxide or chloride (Pre)ligands for cross-couplings of unactivated alkyl chlorides
Ackermann, Lutz,Kapdi, Anant R.,Schulzke, Carola
supporting information; experimental part, p. 2298 - 2301 (2010/08/05)
In situ generated and crystallographically well-defined, isolated palladium complexes derived from seven novel air-stable secondary phosphine oxides or chlorides enabled challenging Kumada-Corriu cross-couplings of unactivated alkyl chlorides bearing β-hy
