Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 11, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202115497
Keywords
Amides; alpha-Aminocarbene; C-H Functionalization; Polyfluoroarenes; Polyfluoroarylation
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Funding
- National Natural Science Foundation of China [21821002, 21903071]
- Shanghai Pujiang Program [19PJ1411500]
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The cross-coupling of amides and polyfluoroarenes through direct C-H functionalization can lead to new carbon-carbon bond-forming methodologies, which have useful applications in synthesis, late-stage functionalization, and generation of molecular diversity.
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.
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