An article Nucleophilic Addition and alpha-C-H Substitution Reactions of an Imine Mediated by Dibutylmagnesium and Organolithium Reagents WOS:000669544500006 published article about ORGANOMETALLIC REAGENTS; ASYMMETRIC ALKYLATION; HYDROBORATION; 1,2-ADDITION; COMPLEXES; ALDEHYDES; EFFICIENT; AMINES; BONDS in [Dang, Yan; Wang, Yalan; Li, Yafei; Xu, Man; Jia, Chaohong; Lu, Yanhua; Zhang, Liang; Li, Yahong] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China; [Xia, Yuanzhi] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China in 2021.0, Cited 36.0. Quality Control of Benzophenone. The Name is Benzophenone. Through research, I have a further understanding and discovery of 119-61-9
A series of nucleophilic addition reactions and alpha-C-H substitution reactions of an imine-containing ligand 2-(2-((((1H-pyrrol-2-yl)methylene)amino)methyl)-1H-pyrrol-1-yl) -N,N-d imethylethan-1-amine (HL1) were reported. The reactions of HL1 with 0.5 and 2 equiv of (Bu2Mg)-Bu-n, respectively, gave two complexes of compositions [Mg(L1)(2)] (1) and [Mg-2(L2)(2)] (2) (H2L2 = N-((1-(2- (dimethylamino) ethyl)-1 H-pyrrol-2-yl) methyl)-1-(1H-pyrrol-2-yl)pentan-1-amine). The nucleophilic addition of (Bu2Mg)-Bu-n to the C=N bond of the HL1 ligand occurred in the process for the formation of 2. Treatment of HL1 with 2 and 1 equiv of (BuLi)-Bu-n generated [Li-2(L3)(2)] (3) (HL3 = 2-(2-(((1-(1H-pyrrol-2-yl)-pentylidene)amino)methyl)-1H-pyrrol-1-yl)-N,N-dimethylethan-1-amine) and [Li-2(L1)(2)] (4). An alpha-C-H substitution of the HC=NR moiety of the HL1 ligand triggered by (BuLi)-Bu-n was discovered in the preparation of 3. The formation of 3 demonstrates a new concept for the C-C coupling that involved inert C-H bond activation of HC=NR skeleton. The reactions of HL1 with MeLi, sec-BuLi, and tert-BuLi, respectively, were also examined. The products for both the nucleophilic addition of organolithium reagents to the C=N bond and alpha-C-H substitution of the HC=NR moiety of the HL1 ligand were determined. The mechanisms for the formations of 2 and 3 were rationalized by DFT calculations. The hydroboration reactions catalyzed by 2 were investigated, and these reactions characterize ample substrate scope, very good yields, and high selectivity.
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Reference:
Thiomorpholine – Wikipedia,
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