4.8 Article

NBE-Controlled Palladium-Catalyzed Interannular Selective C-H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2-Acetamides

Journal

ORGANIC LETTERS
Volume 21, Issue 8, Pages 2718-2722

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00690

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Funding

  1. National Natural Science Foundation of China [21572051, 21602057]
  2. Opening Fund of Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University [KLCBTCMR201707, KLCBTCMR201708]
  3. Science and Technology Planning Project of Hunan Province [2018TP1017]

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A novel palladium-catalyzed interannular selective C-H silylation of 1,1'-biaryl-2-acetamides is described. The combination of palladium catalyst with copper oxidant enables meta- or ortho-selective C-H silylation by employing hexamethyldisilane as a trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent silicon-containing 1,1'-biaryl-2-acetamides.

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