473790
trans-2-Phenylvinylboronic acid
97%
Synonym(s):
(E)-2-phenyl-Etheneboronic acid, (E)-Phenylethenylboronic acid, (E)-Styreneboronic acid, (E)-Styrylboronic acid, trans-(2-Phenylethenyl)boronic acid, trans-Phenylvinyl boronic acid
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All Photos(2)
About This Item
Linear Formula:
C6H5CH=CHB(OH)2
CAS Number:
Molecular Weight:
147.97
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
mp
146-156 °C (lit.)
functional group
phenyl
SMILES string
OB(O)\C=C\c1ccccc1
InChI
1S/C8H9BO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7,10-11H/b7-6+
InChI key
VKIJXFIYBAYHOE-VOTSOKGWSA-N
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Related Categories
Application
Reagent used for
Reagent used in Preparation of
- Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions[1]
- Rhodium (Rh)-catalyzed intramolecular amination of aryl azides[2]
- Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction[3]
- Copper (Cu)-mediated cyanation[4]
- Rhodium (Rh)-catalyzed asymmetric addition[5]
- Diastereoselective synthesis via iridium (Ir)-catalyzed addition[6]
- Palladium (Pd)-catalyzed cascade cyclization[7]
Reagent used in Preparation of
Other Notes
Contains varying amounts of anhydride
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, J. E.
Tetrahedron Letters, 53, 2308-2311 (2012)
Rebecca L Greenaway et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(51), 14366-14370 (2011-11-25)
Cascade reactions: A modular assembly of azabicycles by using a cascade cyclization/Suzuki coupling/6π-electrocyclization of bromoenynamides is reported. The reaction offers a wide substituent scope on the bicyclic aminodiene products, which can be selectively oxidized as a general approach to aromatic
Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids
Hirokazu Tsukamoto, et al.
Chemical Communications (Cambridge, England), 1200-1201 (2004)
Hao Yang et al.
Journal of the American Chemical Society, 129(5), 1132-1140 (2007-02-01)
alpha-Amino acid thiol esters derived from N-protected mono-, di-, and tripeptides couple with aryl, pi-electron-rich heteroaryl, or alkenyl boronic acids in the presence of stoichiometric Cu(I) thiophene-2-carboxylate and catalytic Pd(2)(dba)(3)/triethylphosphite to generate the corresponding N-protected peptidyl ketones in good-to-excellent yields
Tomohiro Iwai et al.
Journal of the American Chemical Society, 134(2), 1268-1274 (2011-12-14)
Iridium complexes show high catalytic activity in intermolecular additions of acid chlorides to terminal alkynes to afford valuable (Z)-β-chloro-α,β-unsaturated ketones. Ligands in the catalytic system play a crucial role in this reaction. An N-heterocyclic carbene (NHC) is an efficient ligand
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