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Nickel-catalyzed reductive cross-coupling of polyfluoroarenes with alkyl electrophiles by site-selective c–f bond activation

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chinese chemical Letters 2022年第9期33卷 4287-4292页

作者： Longlong Xi Liting Du Zhuangzhi Shi State Key Laboratory of coordination chemistry Chemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210093China Advanced Analysis and Testing center Nanjing Forestry UniversityNanjing 210037China

A nickel-catalyzed reductive cross-coupling reactions between polyfluoroarenes and alkyl electrophiles is reported to access substituted fluoroarenes through chelation-assisted c–f activation.Diverse primary and secondary alkyl(pseudo)halides can be employed to couple with polyfluoroarenes,showing excellent regioselectivity.furthermore,the nickel-catalyzed asymmetric cross-coupling of polyfluoroarenes with racemic alkyl halides is preliminarily explored.In addition,the practicability of the title transformation is also demonstrated by total synthesis of losmapimod and an analog as key steps.The developed method exhibits many advantages,including economic catalytic systems,commercially available alkyl electrophiles,and lack of sensitive organometallic reagents.

关键词： Polyfluoroarenes Nickel Alkylation cross-coupling c-f activation

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Electrochemical Mono-Deuterodefluorination of Trifluoromethyl Aromatic compounds with Deuterium Oxide

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ccS chemistry 2024年第1期6卷 230-240页

作者： Jie Sheng Xu cheng Institute of chemistry and Biomedical Sciences Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023 State Key Laboratory of Elemento-Organic chemistry Nankai UniversityTianjin 30071

The deuterodifluoromethyl group cf_(2)D combines the structural features of cf_(3) and cD_(3) groups,finding wide applications in diverse pharmaceutical entities.In this work,the electrochemical monodeuterodefluorination of Ar-cf_(3) to Ar-cf_(2)D is achieved with an unreported deuterium atom transfer-coupled electron transfer pathway using D_(2)O as the only D source for the first time.A series of Ar-cf_(3) substances,including commercial pharmaceuticals,were converted to corresponding cf_(2)D products in up to 91% yield and 97% D-incorporation.A variety of functional groups,including pyridine,pyrrole,furan,thiophene,borate,thio ether,amine,amide,sulfonamide,and halide,are well tolerated in this protocol.t-BuOLi was an essential reagent to achieve chemoselective mono-defluorination.

关键词： electrochemistry c-f activation fluorinecontaining drugs deuterated drugs deuterium oxide

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三甲基膦支持的镍化合物对亚胺中氮-氢键的活化和功能化(英文)

三甲基膦支持的镍化合物对亚胺中氮-氢键的活化和功能化(英文)

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中国化学会全国第十一届有机合成化学学术研讨会

作者：王麟孙宏建李晓燕山东大学化学与化工学院

The activation and fiinctionalization of N-H bond by transition-metal complexes has been widely applied in modern synthetic organic chemistry. Besides precious metal complexes, more and more inexpensive and eco-friendly metal complexes such as iron, cobalt and nickel complexes are utilized in the activation of N-H bond. In our earlier work, the N-H bonds contained in benzamide and 2-aminobenzophenone were successfully activated by electron-rich co and Ni complexes.1’2 As a continuation, the reactions of a series of arylmethanimines with NiclMe(PMe3)2 and NiMe2(PMe3)3 are discussed in this paper.The reactions of NiclMe(PMe3)2 with fluorinated imine ligands 1 and 2 gave rise to complexes 3 and 4 as five-coordinated trigonal bipyramids(Scheme 1). The imine ligands interacted with the Ni centre via 7i-coordination and N-H bond was not cleavaged sufficiently. Due to the influence of steric hindrance, imine ligand 5 could not react with NiclMe(PMe3)2. The activation of N-H bond was also realized from the reactions of NiMe2(PMe3)3 with imine ligangs 1,2,5,6 and 7. As a result, four-coordinated binuclear nickel complexes 8,9,10,11 and 12 were obtained in the yields of 561%(Scheme 2). The structures showed that two nickel atoms were bridged by the N atom.A more interesting phenomenon was observed from the reaction of imine ligand 5 with NiMe2(PMe3)3 with complex 10 as main product and compound 13 as byproduct. The carbon-nitrogen coupling product 15 became the main product from the reaction of ligand 14 with NiMe2(PMe3)3. In addition, the double substituted product 16 was observed via MS(Scheme 3). This kind of coupling product was not obtained from other reaction of imine and NiMe2(PMe3)3.This suggests that the steric hindrance might be the key point to influence the reactions.

关键词： N-H activation binuclear nickel complexes c-f activation c,N-coupling

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