MIDA boronates: powerful tool for organic synthesis

The transition-metal-catalyzed cross-coupling reactions are powerful tools for the formation of carbon–carbon bonds. Among these transformations, the Suzuki–Miyaura reaction, which is the transition-metal-catalyzed cross-coupling between an organo-boron compound and an organic (pseudo)halide, has become the most attractive method since its discovery in 1979. While many organo-boron compounds have been discovered, N-methyliminodiacetic acid MIDA boronates represent tremendously useful building blocks for the Suzuki–Miyaura cross-coupling that has been successfully applied to sequential synthesis of various natural product motifs.

Features of MIDA boronates:

• Stable to benchtop storage under air;
• Compatible with common functional groups (FG);
• Compatible with wide range of common synthetic reagents;
• Tolerate harsh reaction conditions (strongly acidic, oxidative, etc.);
• Easily hydrolyzed using mild conditions;
• Compatible with chromatography.