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New aryl(mesityl)iodonium salts are synthesized via boron-iodane exchange. Modifications improve yield and reaction speed, revealing a transmetallation mechanism for these versatile aryl transfer reagents.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Aryl transfer reagents are crucial in organic synthesis.
  • Aryl(mesityl)iodonium salts are versatile reagents for aryl group transfer.
  • Previous synthesis methods had limitations in yield and reaction time.

Purpose of the Study:

  • To develop an improved synthesis of aryl(mesityl)iodonium salts.
  • To enhance the efficiency and speed of aryl transfer reactions.
  • To elucidate the reaction mechanism.

Main Methods:

  • Synthesis of aryl(mesityl)iodonium salts via boron-iodane exchange.
  • Modification of both nucleophilic (aryl boron) and electrophilic (mesityl-λ³-iodane) components.
  • Mechanistic studies including kinetic analysis.

Main Results:

  • Achieved improved yields and significantly faster reaction times compared to existing methods.
  • Demonstrated the versatility of the modified aryl transfer reagents.
  • Mechanistic investigations indicated a transmetallation pathway, distinct from SEAr.

Conclusions:

  • The modified boron-iodane exchange offers a superior route to aryl(mesityl)iodonium salts.
  • These reagents facilitate efficient aryl transfer reactions.
  • The reaction proceeds via a transmetallation mechanism, providing new mechanistic insights.