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473790

Sigma-Aldrich

trans-2-Phenylvinylboronic acid

97%

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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
Linear Formula:
C6H5CH=CHB(OH)2
CAS Number:
6783-05-7
Molecular Weight:
147.97
MDL number:
MFCD00963621
UNSPSC Code:
12352103
PubChem Substance ID:
24870932
NACRES:
NA.22

Quality Level

100

assay

97%

mp

146-156 °C (lit.)

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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Application

Reagent used for
  • Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions
  • Rhodium (Rh)-catalyzed intramolecular amination of aryl azides
  • Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction
  • Copper (Cu)-mediated cyanation
  • Rhodium (Rh)-catalyzed asymmetric addition
  • Diastereoselective synthesis via iridium (Ir)-catalyzed addition
  • Palladium (Pd)-catalyzed cascade cyclization

Reagent used in Preparation of
  • Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction
  • Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization

Other Notes

Contains varying amounts of anhydride

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

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)
Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
Lu, G-P.; et al.
The Journal of Organic Chemistry, 77, 370-3703 (2012)
Xiangqing Feng et al.
Organic letters, 14(2), 624-627 (2012-01-12)
This paper describes a Rh(I)-catalyzed highly efficient and enantioselective 1,2-addition of arylboronic acids to α-diketones with the use of a simple sulfur-alkene hybrid ligand. With as low as a 0.1 mol % catalyst loading, a variety of optically active α-hydroxyketones
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