264144-59-4

Usage

Uses

Used in Pharmaceutical Industry:
CIS-STILBENEBORONIC ACID PINACOL ESTER is used as a synthetic intermediate for the development of pharmaceutical compounds. Its ability to form carbon-carbon bonds through cross-coupling reactions allows for the creation of complex molecular structures, contributing to the discovery and synthesis of novel drugs.
Used in Agrochemical Industry:
In the agrochemical industry, CIS-STILBENEBORONIC ACID PINACOL ESTER is used as a building block for the synthesis of agrochemicals. Its reactivity in cross-coupling reactions enables the production of new and improved pesticides, herbicides, and other agricultural chemicals.
Used in Materials Science:
CIS-STILBENEBORONIC ACID PINACOL ESTER is used as a precursor in the development of new materials. Its structural properties and reactivity make it suitable for the synthesis of advanced materials with unique properties, such as high strength, lightweight, or specific optical characteristics.
Used in Organic Chemistry Research:
As a key compound in organic chemistry, CIS-STILBENEBORONIC ACID PINACOL ESTER is used in research to explore new reaction pathways, develop innovative synthetic methods, and understand the fundamental principles of cross-coupling reactions. Its stability and effectiveness in catalyzing reactions make it an essential tool for advancing the field of organic chemistry.

InChI:InChI=1/C20H23BO2/c1-19(2)20(3,4)23-21(22-19)18(17-13-9-6-10-14-17)15-16-11-7-5-8-12-16/h5-15H,1-4H3/b18-15+

Upstream product

• 501-65-5 diphenyl acetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-86-1 bromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 591-50-4 iodobenzene 
• 7732-18-5 water 
• 536-74-3 phenylacetylene 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 19816-85-4 N'-(1,2-diphenylethylidene)-4-methylbenzenesulfonohydrazide 
• 451-40-1 phenyl benzyl ketone 
• 645-49-8 cis-stilben 
• 51901-85-0 bromocatecholborane 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 645-49-8 cis-stilben 
• 451-40-1 phenyl benzyl ketone 
• 1020073-95-3 (E)-4-(1,2-diphenylvinyl)benzonitrile 
• 119379-68-9 (E)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene 
• 134-81-6 benzil 
• 1414852-68-8 2-benzoyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 602-15-3 9,10-diphenylphenanthrene 

Relevant academic research and scientific papers

Palladium-Catalyzed [3 + 2] Annulation of Alkynes with Concomitant Aromatic Ring Expansion: A Concise Approach to (Pseudo)azulenes

The construction of (pseudo)azulenes represents an appealing yet challenging task in organic synthetic chemistry. Herein, we disclose a palladium-catalyzed [3 + 2] annulation technique of alkynes with concomitant aromatic ring expansion driven by a diboron reagent and iodide, affording a concise approach to azulenes (7-fused-5 bicycle) and pseudoazulenes (6-fused-5 bicycle). Compared with the documented synthetic strategies, the route to (pseudo)azulenes developed herein is applicable for both homo- and cross-annulation processes and exhibits a broad substrate scope. It is worth noting that this transformation is not only suitable for the ring expansion of the phenyl moiety to afford azulenes but also applicable to the ring expansion of the electron-rich five-membered heterocycles to deliver pseudoazulenes. Experimental and computational investigations on the mechanism support the formal trans-palladium-boration across the alkyne, cis-addition of the alkyne, dearomative spiroannulation, and aromatic ring expansion process.

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

Cobalt-Catalyzed Hydroboration of Terminal and Internal Alkynes

A novel methodology to access synthetically versatile vinylboronic esters through a ligand-controlled cobalt-catalyzed hydroboration of terminal and internal alkynes is reported. The approach relies on the in situ reduction of Co(II) by H-BPin in the presence of bisphosphine ligands generating catalytically active Co(I) hydride complexes. This procedure avoids the use of stoichiometric amounts of base, and no boron-containing byproducts are generated which is translated into high functional group tolerance and atom economy.

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. (Figure presented.).

Synthesis of Alkenylboronates from N-Tosylhydrazones through Palladium-Catalyzed Carbene Migratory Insertion

The palladium-catalyzed oxidative borylation reaction of N-tosylhydrazones has been developed. The reaction features mild conditions, broad substrate scope, and good functional group tolerance. It thus represents a highly efficient and practical method for the synthesis of di-, tri-, and tetrasubstituted alkenylboronates from readily available N-tosylhydrazones. One-pot Suzuki coupling and other transformations highlight the synthetic utility of the approach. DFT calculations have revealed that palladium-carbene formation and subsequent boryl migratory insertion are the key steps in the catalytic cycle. The high stereoselectivity observed in the formation of trisubstituted alkenylboronates has been explained by distortion-interaction analysis and NBO analysis.

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Selective hydroboration of alkynes via multisite synergistic catalysis by PCN-222(Cu)

Zirconium-based porphyrinic MOFs (PMOFs, MOF = metal-organic framework) have gained considerable attention in the field of electric/thermo/photo-catalysis as heterogeneous single-site catalysts; however, the study on multisite synergistic catalysis of PMO

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.