MIDA Boronates for Suzuki–Miyaura Cross-Couplings: Advantages

By: Aaron Thornton, ChemFiles Volume 11 Article 1

Aaron Thornton, Ph.D.
Product Manager
aaron.thornton@sial.com

Professor Martin Burke and coworkers recently prepared retinal using key MIDA building block BB1 in iterative Suzuki-Miyaura cross coupling reactions (Scheme 1). The MIDA unit of BB1 is unreactive under these conditions, allowing for the selective cross-coupling of BB1 with triene (1). Subsequent hydrolysis of the MIDA unit of (2) followed by a second Suzuki-Miyaura reaction provided all-trans-retinal.

Scheme 1: Iterative Suzuki-Miyaura cross-couplings in the synthesis of all-trans-retinal.(703478)


The many advantages of the MIDA boronate platform include air and moisture stability, stability under anhydrous cross-coupling conditions, compatibility with a range of common and harsh reagents, solubility in various organic solvents, silica gel compatibility, and the ability to undergo slow release cross-couplings.

MIDA Boronates from Aldrich:

(697311), (698709), (700231),
(707252), (704415), (708828
)


For complete list of MIDA boronates available from Aldrich Chemistry, visit Aldrich.com/mida

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Materials

     

References

  1. Lee, S. J. et al. J. Am. Chem. Soc. 2008, 130, 466.

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