4.8 Article

Rh(III)-Catalyzed meta-C-H Olefination Directed by a Nitrile Template

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 6, Pages 2200-2203

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b13269

Keywords

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Funding

  1. National Natural Science Foundation of China [21201100, 21671097, 21331002]
  2. National Science Foundation [CHE-1465292]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1465292] Funding Source: National Science Foundation

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A range of Rh(III)-catalyzed ortho-C-H functionalizations have been developed; however, extension of this reactivity to remote C-H functionalizations through large-ring rhodacyclic intermediates has yet to be demonstrated. Herein we report the first example of the use of a U-shaped nitrile template to direct Rh(III)catalyzed remote meta-C-H activation via a postulated 12-membered macrocyclic intermediate. Because the ligands used for Rh(III) catalysts are significantly different from those of Pd(II) catalysts, this offers new opportunities for future development of ligand-promoted meta-C-H activation reactions.

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