148914-43-6

Basic information

• Product Name: (benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene
• Synonyms: (benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene
• CAS NO: 148914-43-6
• Molecular Weight: 252.077
• Mol File: 148914-43-6.mol

Chemical Properties

• CAS DataBase Reference: (benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene(CAS DataBase Reference)
• NIST Chemistry Reference: (benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene(148914-43-6)
• EPA Substance Registry System: (benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene(148914-43-6)

Safety Data

• Hazardous Substances Data: 148914-43-6(Hazardous Substances Data)

Upstream product

• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 696-62-8 para-iodoanisole 
• 637-69-4 4-Methoxystyrene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 768-60-5 4-methoxyphenylacetylen 

Downstream Products

• 1147458-99-8 (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 72316-18-8 (E)-2-(4-methoxyphenyl)vinylboronic acid 
• 148914-42-5 4-MeOC₆H₄CH(Bcat)CH₂(Bcat) 

Relevant articles and documents

Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol

Using the previously designed biphenyl-2-ylphosphine ligand, featuring a remote tertiary amino group, the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general-base catalyst for promoting this novel gold catalysis with good efficiency.

Asymmetric Synthesis of α-Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination

A copper-catalyzed regio- and enantioselective hydroamination of alkenyl dan boronates (dan =1,8-diaminonaphthyl) with hydrosilanes and hydroxylamines proceeds to deliver the chiral α-aminoboronic acids in good yields with high enantiomeric ratios. The ke

Anomalies in the stereoselectivity of the petasis reaction using styrenyl boronic acids

The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives. CSIRO 2011.

Synthesis and structure of indenyl rhodium(I) complexes containing unsaturated phosphines: Catalyst precursors for alkene hydroboration

The indenyl compound (η5-C9H7)Rh(coe) 2 (1, coe = cis-cyclooctene) has been prepared as a thermally stable alternative to the diethylene derivative (η5-C9H 7)Rh(η2-H2CCH2)2. Compound 1 reacts with unsaturated phosphines Ph2PR (R = CHCH 2, 2; CH2CHCH2, 3; and CC-tert-Bu, 4) to give complexes of the type (η5-C9H7)Rh(Ph 2PR)2, where bonding occurs through the phosphorus atom. Addition of Ph2PCCPPh2 to 1 gave the dimer [(η5-C9H7)Rh(μ-Ph2PCCPPh 2)]2 (5). Solution and solid state data showed that these new phosphine complexes have only a moderate amount of distortion within the indenyl ring. These compounds were found to catalyse the hydroboration of vinylarenes and the first example of an internal hydroboration of diphenylvinylphosphine has been reported. The Royal Society of Chemistry 2009.

Hydroboration of vinyl arenes using SiO2-supported rhodium catalysts

The metal-catalyzed hydroboration of vinyl arenes using catecholborane (HBcat) and pinacolborane (HBpin) has been examined with SiO2- supported rhodium catalysts. Reactions with simple vinyl arenes (ArCH=CH 2) and HBcat using Rh(acac

Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands

Addition of o-C6H4NCH=NAr to Rh(coe) 2(acac) (coe = cis-cyclooctene, acac = acetylacetonato) gave several new iminopyridine rhodium(I) complexes of the type Rh(acac)(κ2- o-C6H4NCH=NAr) (1a Ar = 4-C6H4-OMe; 1b Ar = 2,6-C6H3-Me2; 1c Ar = 2,6-C 6H3-Et2; 1d Ar = 2,6-C6H 3-i-Pr2). All new rhodium complexes have been characterized by a number of physical methods, including multinuclear NMR spectroscopy and X-ray diffraction studies for 1b and 1c. Addition of CHCl 3 to 1a afforded the corresponding rhodium(III) complex trans-Rh(κ2-o-C6H4NCH=NAr)(CHCl 2)(Cl)(acac) (2). Addition of B2cat3 (cat = 1,2-O2C6H4) to 1 gave zwitterionic Rh(η6-catBcat)(κ2-o-C6H 4NCH=NAr) (3). The molecular structure of 3b has been confirmed by a single crystal X-ray diffraction study and shows that the N2Rh fragment is bound to the catBcat anion via one of the catecholato groups in a η6-fashion. These complexes have also been examined for their ability to catalyze the hydroboration of a series of vinylarenes. Reactions using catecholborane and pinacolborane seem to proceed largely through a dehydrogenative borylation mechanism to give a number of boronated products.

The active role of NHC ligands in platinum-mediated tandem hydroboration-cross coupling reactions

Stable N-heterocyclic platinum-carbene complexes are the first example of platinum-mediated regioselective H-B addition to vinylarenes and alkynes, allowing consecutive cross coupling reactions with the same catalytic system. The Royal Society of Chemistry.

Rhodium(I) catalysed diboration of (E)-styrylboronate esters: Molecular structures of (E)-p-MeO-C6H4-CH = CH-B(1,2-O2C6H4) and p-MeO-C6H4-CH2C {B(1,2-O2C

Diboration of the styrylboronate esters (E)-p-R-C6H4-CH=CH-Bcat (1) (R = H, (1a) MeO (1b); cat = 1,2-O2C6H4), with B2cat2 in the presence of a variety of rhodium phosphine cataly

Enhanced regioselectivity of rhodium-catalysed alkene hydroboration in supercritical carbon dioxide

Catalysed alkene hydroboration proceeds in supercritical CO2 with several rhodium(I) complexes using tunable fluorinated ligands and shows higher regioselectivity relative to tetrahydrofuran or perfluoromethylcyclohexane.

Vinylborane formation in rhodium-catalyzed hydroboration of vinylarenes. Mechanism versus borane structure and relationship to silation

Attempted catalytic hydroboration of (4-methoxyphenyl)ethene 1 with R,R-3-isopropyl-4-methyl-5-phenyl-1,3,2-oxazaborolidine 6 proceeded extremely slowly relative to the 3-methyl analog 2 derived from φ-ephedrine when diphosphinerhodium complexes were employed. With phosphine-free rhodium catalysts, especially the 4-methoxy-phenylethene complex 7, the reaction proceeded rapidly and quantitatively to give only the corresponding (E)-vinylborane 9 and 4-methoxyethylbenzene 8 in equimolar amounts. Isotopic labeling and kinetic studies demonstrated that this reaction pathway is initiated by the formation of a rhodium hydride with subsequent reversible and regiospecific H-transfer to the terminal carbon, giving an intermediate which adds the borane and then eliminates the hydrocarbon product. Further migration of the secondary borane fragment from rhodium to the β-carbon of the coordinated olefin occurs, followed by Rh-H β-elimination which produces the vinylborane product and regenerates the initial catalytic species. When the same catalytic reaction is carried out employing catecholborane in place of the oxazaborolidine, an exceedingly rapid turnover occurs. The products are again 4-methoxyethylbenzene and the (E)-vinylborane 23 but accompanied by the primary borane 24 in proportions which vary with the experimental conditions. None of the secondary borane, which is the exclusive product when pure ClRh(PPh3)3 is employed as catalyst, is formed. The product variation as a function of initial reactant concentration was fitted to a model in which the rhodium-borane intermediate in the catalytic cycle undergoes two competing reactions-β-elimination of Rh-H versus addition of a further molecule of catecholborane. The model demonstrates that a kinetic isotope effect of 3.4 operates in the β-elimination step, but none is evident in the addition of catecholborane B-D to rhodium. A similar analysis was successfully applied to the catalytic hydrosilylation of 4-methoxystyrene, with HSiEt3, again employing the phosphine-free rhodium catalyst 7; the product distribution between primary silane 29 and vinylsilane 28 was successfully predicted. The results intimate that silation (i.e., the formation of vinylsilanes under the conditions of catalytic hydrosilylation) can best be explained by a Rh-H based mechanistic model rather than the commonly assumed variant on the Chalk-Harrod catalytic cycle. They provide an explanation for the "oxygen effect" on the rate of Rh-catalyzed hydrosilylations.