1073339-17-9

Basic information

• Product Name: 2-(2,3-difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2,3-difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;2,3-Difluorophenylboronic acid pinacol ester
• CAS NO: 1073339-17-9
• Molecular Formula: C12H15BF2O2
• Molecular Weight: 240.0541064
• Mol File: 1073339-17-9.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,3-difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,3-difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(1073339-17-9)
• EPA Substance Registry System: 2-(2,3-difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(1073339-17-9)

Safety Data

• Hazardous Substances Data: 1073339-17-9(Hazardous Substances Data)

Usage

General Description

2-(2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound with the molecular formula C13H16BF2O2. It is a boronic ester derivative, which is commonly used in organic synthesis and medicinal chemistry. 2-(2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a versatile building block for the synthesis of pharmaceuticals, agrochemicals, and materials due to its unique reactivity with various functional groups. Its boron atom serves as a useful reactive site for Suzuki-Miyaura coupling reactions, allowing for the formation of carbon-carbon bonds. Additionally, this compound has also shown potential as a fluorine-18 labeled agent for positron emission tomography (PET) imaging due to its high stability and selectivity towards specific biological targets.

Upstream product

• 36556-47-5 3-chloro-1,2-difluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 367-11-3 ortho-difluorobenzene 
• 38573-88-5 1-bromo-2,3-difluorobenzene 
• 1489-53-8 1,2,3-trifluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1073339-12-4 C₁₂H₁₄BBrF₂O₂ 
• 348-61-8 1-bromo-3,4-difluorobenzene 

Relevant articles and documents

Selective Photocatalytic C-F Borylation of Polyfluoroarenes by Rh/Ni Dual Catalysis Providing Valuable Fluorinated Arylboronate Esters

A highly selective and general photocatalytic C-F borylation protocol that employs a rhodium biphenyl complex as a triplet sensitizer and the nickel catalyst [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the C-F bond activation and defluoroborylation process is reported. This tandem catalyst system operates with visible (blue, 400 nm) light and achieves borylation of a wide range of fluoroarenes with B2pin2 at room temperature in excellent yields and with high selectivity. Direct irradiation of the intermediary C-F bond oxidative addition product trans-[NiF(ArF)(IMes)2] leads to very fast decomposition when B2pin2 is present. This destructive pathway can be bypassed by indirect excitation of the triplet states of the nickel(II) complex via the photoexcited rhodium biphenyl complex. Mechanistic studies suggest that the exceptionally long-lived triplet excited state of the Rh biphenyl complex used as the photosensitizer allows for efficient triplet energy transfer to trans-[NiF(ArF)(IMes)2], which leads to dissociation of one of the NHC ligands. This contrasts with the majority of current photocatalytic transformations, which employ transition metals as excited state single electron transfer agents. We have previously reported that C(arene)-F bond activation with [Ni(IMes)2] is facile at room temperature, but that the transmetalation step with B2pin2 is associated with a high energy barrier. Thus, this triplet energy transfer ultimately leads to a greatly enhanced rate constant for the transmetalation step and thus for the whole borylation process. While addition of a fluoride source such as CsF enhances the yield, it is not absolutely required. We attribute this yield-enhancing effect to (i) formation of an anionic adduct of B2pin2, i.e., FB2pin2-, as an efficient, much more nucleophilic {Bpin-} transfer reagent for the borylation/transmetalation process, and/or (ii) trapping of the Lewis acidic side product FBpin by formation of [F2Bpin]- to avoid the formation of a significant amount of NHC-FBpin and consequently decomposition of {Ni(NHC)2} species in the reaction mixture.

C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes

Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.

Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage

The [Ni(IMes)2]-catalyzed transformation of fluoroarenes into arylboronic acid pinacol esters via C-F bond activation and transmetalation with bis(pinacolato)diboron (B2pin2) is reported. Various partially fluorinated arenes with different degrees of fluorination were converted into their corresponding boronate esters.

Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes

We report herein a mild procedure for the copper-catalyzed oxidative cross-coupling of electron-deficient polyfluorophenylboronate esters with terminal alkynes. This method displays good functional group tolerance and broad substrate scope, generating cro