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  Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent

Boursalian, G. B., Ngai, M.-Y., Hojczyk, K. N., & Ritter, T. (2013). Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent. Journal of the American Chemical Society, 135(36), 13278-13281. doi: 10.1021/ja4064926.

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 Creators:
Boursalian, Gregory B.1, Author
Ngai, Ming-Yu1, Author
Hojczyk, Katarzyna N1, Author
Ritter, Tobias1, Author           
Affiliations:
1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA), ou_persistent22              

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Free keywords: N-FLUOROBENZENESULFONIMIDE; INTERMOLECULAR AMINATION; AROMATIC SUBSTITUTION; AMBIENT-TEMPERATURE; NITRENE INSERTION; BONDS; PALLADIUM(IV); ACTIVATION; AMIDATION; COMPLEXES
 Abstract: An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.

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Language(s): eng - English
 Dates: 2013-06-262013-09-032013-09-11
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja4064926
 Degree: -

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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC 20036 : ACS publications
Pages: 4 Volume / Issue: 135 (36) Sequence Number: - Start / End Page: 13278 - 13281 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870