60263-44-7Relevant articles and documents
C2-selective alkylation of pyridines by rhodium–aluminum complexes
Aso, Koki,Hara, Naofumi,Li, Qiao-Zhi,Nakao, Yoshiaki,Sakaki, Shigeyoshi
supporting information, (2021/08/06)
A C2- and mono-selective alkylation of various pyridines and azines with unactivated alkenes and vinylarenes using a heterobimetallic Rh–Al catalyst is reported. The use of aliphatic alkenes exclusively affords the linear alkylation products, while vinylarenes mainly afford branched alkylation products. The details of the reaction mechanism are revealed by DFT calculations: the reductive elimination of the products is rate-determining, which is consistent with the experimental results. The origin of the linear/branched selectivity is elucidated based on deformation/interaction analysis.
Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions
Pang, Haobo,Wang, Ye,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 17117 - 17124 (2019/11/03)
The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene. The coupling only occurs in an aqueous micellar medium, where a radical process is likely, supported by several control experiments. A mechanism based on these data is proposed.
Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation
Lewis, Jared C.,Bergman, Robert G.,Ellman, Jonathan A.
, p. 5332 - 5333 (2008/02/04)
The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work. Copyright