280116-83-8Relevant articles and documents
Base-Mediated Amination of Alcohols Using Amidines
Chen, Jianbin,Fang, Yanchen,Jia, Xiaofei,Jiang, Shaohua,Li, Zehua,Liang, Zuyu,Lu, Fenghong,Qi, Shuo,Ren, Chaoyu,Yu, Shuangming,Zhang, Chunyan,Zhang, Guoying,Zhang, Sheng
, p. 7728 - 7738 (2020/07/15)
Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.
Zinc-Catalyzed N-Alkylation of Aromatic Amines with Alcohols: A Ligand-Free Approach
Sankar, Velayudham,Kathiresan, Murugavel,Sivakumar, Bitragunta,Mannathan, Subramaniyan
supporting information, p. 4409 - 4414 (2020/09/01)
An efficient zinc-catalyzed N-alkylation reaction of aromatic amines was achieved using aliphatic, aromatic, and heteroaromatic alcohols as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N-alkylation reaction and furnished the corresponding monoalkylated products in good to excellent yields. The application of the reaction is also further demonstrated by the synthesis of a 2-phenylquinoline derivative from acetophenone and 2-aminobenzyl alcohol. Deuterium labeling experiments show that the reaction proceeds via a borrowing hydrogen process. (Figure presented.).
Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines
Keylor, Mitchell H.,Niemeyer, Zachary L.,Sigman, Matthew S.,Tan, Kian L.
supporting information, p. 10613 - 10616 (2017/08/15)
A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis[bis(dimethylamino)phosphino]ferrocene "DMAPF", a readily available yet previously unutilized diphosphine, as a uniquely effective ligand for this transformation.