870195-94-1

Usage

Uses

Used in Organic Synthesis:
2-Chlorophenylboronic acid, pinacol ester is used as a reagent in palladium-catalyzed cross-coupling reactions for the formation of carbon-carbon bonds. This application is crucial in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 2-chlorophenylboronic acid, pinacol ester is used as a building block for the development of new drugs. Its reactivity in cross-coupling reactions allows for the creation of diverse molecular structures with potential therapeutic properties.
Used in Agricultural Chemistry:
Similarly, in agricultural chemistry, 2-chlorophenylboronic acid, pinacol ester is utilized as a precursor in the synthesis of agrochemicals. Its involvement in cross-coupling reactions enables the production of novel compounds with pesticidal or herbicidal activities, contributing to the development of more effective and environmentally friendly crop protection agents.

InChI:InChI=1/C12H16BClO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,1-4H3

Upstream product

• 95-50-1 1,2-dichloro-benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-90-7 chlorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 694-80-4 2-bromo-1-chlorobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 6104-93-4 2-(2-chloro-phenyl)-benzo[1,3,2]dioxaborole 
• 95-51-2 o-chloroaniline 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 22092-92-8 diisopropopylaminoborane 
• 615-41-8 2-iodochlorobenzene 
• 95-49-8 2-methylchlorobenzene 
• 17733-22-1 2-chlorothioanisole 

Downstream Products

• 1073629-69-2 6-{[6-(2-chlorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester 
• 1341126-06-4 2-[2-(2,2-difluorovinyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1342256-22-7 (F₃B)C₆H₄(CHCF₂)^(1-)*K⁽¹⁺⁾=K[(F₃B)C₆H₄(CHCF₂)] 
• 95-51-2 o-chloroaniline 
• 217-59-4 triphenylene 
• 95-57-8 2-monochlorophenol 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Borylation of Diazonium Salts by Highly Emissive and Crystalline Carbon Dots in Water

Efficient borylation reaction of diazonium salts in water is realized for the first time by using easily prepared, highly emissive and crystalline carbon dots. Electron-donating and electron-withdrawing groups on diazonium salts were well tolerated with moderate to good conversion efficiency. Compared with widely used metal complexes, organic dyes and quantum dots, the approach presented herein uses carbon dots, which are nontoxic and possess good biological and medicinal compatibility and high reactivity. Therefore, this approach presents a new prospective use for carbon dots in green chemistry.

Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron

Room temperature Pd(0)/Ad3P-catalyzed cross-coupling reactions of aryl chlorides with bis(pinacolato)diboron are described. The Pd(0)/Ad3P catalyst, generated from Ad3P-coordinated acetanilide-based palladacycle complex, proved to be an efficient catalyst system for the Miyaura borylation reactions of a variety of aryl chlorides with bis(pinacolato)diboron. The mild reaction condition, the easy availability of the catalyst and good coupling yields make these reactions potentially useful in organic synthesis.

Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light

Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the boron source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light

We developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.