4.8 Article

Direct C-H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 38, Pages 13194-13196

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja1066459

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Funding

  1. NIH/NIGMS [GM-073949]
  2. NSF
  3. Japan Society for the Promotion of Science (JSPS)
  4. Amgen
  5. Bristol-Myers Squibb

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A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate cooxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

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