914675-52-8

Basic information

• Product Name: Biphenyl-2-boronic acid pinaco
• Synonyms: Biphenyl-2-boronic acid pinaco;Biphenyl-2-boronic acid pinacol ester, 97%
• CAS NO: 914675-52-8
• Molecular Formula: C18H21BO2
• Molecular Weight: 280.173
• Mol File: 914675-52-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 76-79℃
• Appearance: /
• Water Solubility: Insoluble in water. Soluble in organic solvents.
• CAS DataBase Reference: Biphenyl-2-boronic acid pinaco(CAS DataBase Reference)
• NIST Chemistry Reference: Biphenyl-2-boronic acid pinaco(914675-52-8)
• EPA Substance Registry System: Biphenyl-2-boronic acid pinaco(914675-52-8)

Safety Data

• Hazardous Substances Data: 914675-52-8(Hazardous Substances Data)

Usage

Description

Biphenyl-2-boronic acid pinacol ester is an organic compound that features a boron atom bonded to a biphenyl group and a pinacol molecule. It is known for its stability and reactivity in various chemical reactions, particularly in the field of organic synthesis.

Uses

Used in Suzuki-Miyaura Cross-Couplings:
Biphenyl-2-boronic acid pinacol ester is used as a key component in Suzuki-Miyaura cross-couplings for enabling the coupling of organoboronic acids that are sensitive to hydrolytic deboronation. This application allows for the formation of carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Stereoselective Reactions:
In the field of asymmetric synthesis, Biphenyl-2-boronic acid pinacol ester serves as a chiral inducer in stereoselective reactions. This application is valuable for the production of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals, agrochemicals, and fragrances. The use of this boronic ester as a chiral inducer helps to control the stereochemistry of the reaction, leading to the formation of desired enantiomers with high selectivity.

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Relevant articles and documents

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.

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.

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.