4.7 Article

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C-H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 3, Pages 561-571

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900989

Keywords

ortho-carbonylation; C-H activation; arene sulfonamide; aryl aldehyde; cyclic N-sulfonyl ketimines

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The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C-H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines.

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