704415
Vinylboronic acid MIDA ester
97%
Synonyme(s) :
6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
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About This Item
Formule empirique (notation de Hill) :
C7H10BNO4
Numéro CAS:
Poids moléculaire :
182.97
Numéro MDL:
Code UNSPSC :
12352103
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Essai
97%
Forme
powder
Pf
152-156 °C
Température de stockage
2-8°C
Chaîne SMILES
CN1CC(=O)OB(OC(=O)C1)C=C
InChI
1S/C7H10BNO4/c1-3-8-12-6(10)4-9(2)5-7(11)13-8/h3H,1,4-5H2,2H3
Clé InChI
MGRQGYAVASCCAK-UHFFFAOYSA-N
Catégories apparentées
Description générale
Vinylboronic acid MIDA ester, like other MIDA boronates, possesses the capacity for controlled, in situ slow-release of boronic acids under aqueous basic conditions allowing the cross-coupling of classically challenging substrates.
Application
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings
Suzuki Cross-Coupling with MIDA Boronates
Suzuki Cross-Coupling with MIDA Boronates
- 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.
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 2
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
Eyeshields, Gloves, type N95 (US)
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A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.
Knapp DM, et al.
Journal of the American Chemical Society, 131(20), 6961-6963 (2009)
Total Synthesis of (−)-Blepharocalyxin D and Analogues.
Cons BD, et al.
Organic Letters, 15(8), 2046-2049 (2013)
(1-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.
Woerly EM, et al.
Tetrahedron, 69(36), 7732-7740 (2013)
Synthesis of trans-2-(Trifluoromethyl) cyclopropanes via Suzuki reactions with an N-methyliminodiacetic acid boronate.
Duncton MA and Singh R.
Organic Letters, 15(17), 4284-4287 (2013)
Vinyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.
Uno BE, et al.
Tetrahedron, 65(16), 3130-3138 (2009)
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