4.2 Article

LEWIS ACID-CATALYZED BORONO-MINISCI REACTIONS OF ARYLBORONIC ACIDS AND HETEROCYCLES

Journal

HETEROCYCLES
Volume 92, Issue 9, Pages 1687-1697

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-16-13506

Keywords

Minisci Reaction; Boronic Acid; Radical; Lewis Acid

Funding

  1. College of Charleston Undergraduate Research and Creative Activities office
  2. Howard Hughes Medical Institute to the College of Charleston as part of their Undergraduate Science Education Competition
  3. College of Charleston
  4. National Science Foundation [1429308]
  5. Division Of Chemistry
  6. Direct For Mathematical & Physical Scien [1429308] Funding Source: National Science Foundation

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A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Bronsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.

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