MIDA Boronates

MIDA boronates represent a new class of caged boronic acids and have proven exceptionally successful in iterative Suzuki-Miyaura cross-couplings. These boronic acid surrogates attenuate the transmetallation between the boronic acid and palladium species; however, deprotection is readily achieved at room temperature under mild aqueous basic conditions using either 1M NaOH, or even NaHCO_3. Additionally, the MIDA boronates are remarkably robust as treatment with various common harsh reagents (e.g. Jones Reagent) provides the transformed derivative with the MIDA component intact.

MIDA Boronates Technology Spotlight provides detailed information including reaction schemes, references and applications.

ChemFiles Vol. 9 No.1, MIDA-protected Boronate Esters, highlights MIDA boronates as useful, reliable, readily deprotectable, and highly robust protecting groups and as intermediates in complex natural product synthesis.

For evidence of the biodegradable nature of the MIDA ligand (M51008), see: Warren, C.B.; Malec, E.J., Science, 176, 277 (1972).

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