Deoxygenative Cross-Coupling of Aromatic Amides with Polyfluoroarenes

被引:42
作者
He, Youliang [1 ]
Wang, Yuxiao [1 ]
Li, Shi-Jun [2 ,3 ]
Lan, Yu [2 ,3 ,4 ,5 ]
Wang, Xiaoming [1 ,6 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[4] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
[5] Chongqing Univ, Chongqing Key Lab Theoret & Computat Chem, Chongqing 400030, Peoples R China
[6] Univ Chinese Acad Sci, Sch Chem & Mat Sci, Hangzhou Inst Adv Study, 1 Sub Lane Xiangshan, Hangzhou 310024, Peoples R China
基金
中国国家自然科学基金;
关键词
Amides; alpha-Aminocarbene; C-H Functionalization; Polyfluoroarenes; Polyfluoroarylation; ELECTRON-TRANSFER REDUCTION; N-HETEROCYCLIC CARBENES; C-H; CHEMOSELECTIVE REDUCTION; SAMARIUM(II) IODIDE; ORGANIC-SYNTHESIS; BOND ACTIVATION; CYCLIZATION CASCADES; METAL; TERTIARY;
D O I
10.1002/anie.202115497
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Considering the ubiquitous nature and ready synthesis of amides, and the great significance of organofluorine-containing species, the cross-coupling of amides and polyfluoroarenes, leading to new carbon-carbon bond-forming methodologies, would find useful applications in synthesis, late-stage functionalization, and rapid generation of molecular diversity. Herein, we present a novel synthesis of alpha-polyfluoroaryl amines via Sm/SmI2-mediated deoxygenative cross-coupling of aromatic amides with polyfluoroarenes through direct C-H functionalization. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of alpha-polyfluoroaryl amines. Combining experimental and theoretical studies, a novel plausible mechanism of the alpha-aminocarbene-mediated C-H insertion has been revealed, which may stimulate future work for the development of novel methods in amine synthesis.
引用
收藏
页数:8
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