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Spatial Anion Control on Palladium for Mild C–H Arylation of Arenes


Dhankhar, Jyoti; González-Fernández, Elisa; Dong, Chao-Chen; Mukhopadhyay, Tufan K; Linden, Anthony; Coric, Ilija (2020). Spatial Anion Control on Palladium for Mild C–H Arylation of Arenes. Journal of the American Chemical Society, 142(45):19040-19046.

Abstract

C–H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C–H bond activation, thereby enabling nondirected C–H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C–H bonds under mild conditions.

Abstract

C–H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C–H bond activation, thereby enabling nondirected C–H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C–H bonds under mild conditions.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Life Sciences > Biochemistry
Physical Sciences > Colloid and Surface Chemistry
Uncontrolled Keywords:Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
Language:English
Date:11 November 2020
Deposited On:02 Feb 2021 16:43
Last Modified:25 Nov 2023 02:47
Publisher:American Chemical Society (ACS)
ISSN:0002-7863
OA Status:Green
Publisher DOI:https://doi.org/10.1021/jacs.0c09611
  • Content: Accepted Version