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Copper activation of boronic acids: factors affecting reactivity

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The generation of nucleophiles from the combination of aryl boronic acids and catalytic amounts of copper salt allows a reactivity distinct from other organometallic species, such as organolithiums or Grignard reagents. Here we examine how the electronic and steric properties of the boronic acid affect the formation of active nucleophiles and their subsequent reactivity with iminium‐type compounds, showing that electron‐rich substrates display reduced reactivity. Copyright © 2014 John Wiley & Sons, Ltd. Here we examine the influence of the electronic nature of aryl boronic acids on the generation of organocopper nucleophiles. It is shown that electron poor substrates are transmetallated more rapidly, helping to explain the higher yields obtained in some addition reactions.
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Keywords: C―C bond formation; catalysis; copper

Document Type: Research Article

Publication date: June 1, 2014

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