Vinylboronic acid MIDA ester

• Vinylboronic acid MIDA ester is an air and chromatographically stable boronic acid surrogate for Suzuki-Miyaura cross-coupling. It can also be used in Heck and oxidative Heck reactions as well as in olefin metathesis to provide the cross-coupled product.• It is compatible with a wide range of common synthetic reagents that allows functionalization to synthesize structurally complex boronic acid surrogates.• It undergoes cyclopropanation and epoxidation to yield corresponding MIDA cyclopropane and oxirane, respectively.• It can be used as one of the major reagents for the scalable synthesis of potent cytotoxin, Leiodermatolide and for the total synthesis of (−)-Blepharocalyxin D.
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplingsSuzuki Cross-Coupling with MIDA Boronates

6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione

2-ethenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

B1(OC(=O)CN(CC(=O)O1)C)C=C

InChI=1S/C7H10BNO4/c1-3-8-12-6(10)4-9(2)5-7(11)13-8/h3H,1,4-5H2,2H3

MGRQGYAVASCCAK-UHFFFAOYSA-N

152-156 °C

Not applicable

97%

2-8°C