MIDA Boronates for Suzuki–Miyaura Cross-Couplings

Aldrich ChemFiles 2010, 10.1, 12.

Burke and coworkers recently prepared retinal using newly-developed methodology, which employs boronic acid surrogates, termed MIDA boronates (retinal synthesis employed key MIDA building block BB1—Scheme 1) in Suzuki-Miyaura cross coupling reactions. The caged boronic acid derivatives are suitable for various historically challenging couplings as well as iterative Suzuki couplings for the preparation of other complex molecules. The many advantages to the MIDA boronate platform include the air and moisture stability, stability under anhydrous cross-coupling conditions, compatibility in the presence of common and harsh reagents, solubility in various organic solvents, silica gel compatibility, and the ability to undergo slow release cross-coupling.

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

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Materials

References

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

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