922706-40-9

Usage

Uses

Used in Academic Research:
2-(9H-Fluoren-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is used as a research chemical for the study of synthetic organic chemistry. Its unique structure and properties make it a valuable tool for understanding the behavior and interactions of organoboron compounds in various chemical reactions.
Used in Laboratory Settings:
In laboratory environments, 2-(9H-Fluoren-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is employed as a reagent or intermediate in the synthesis of more complex organic molecules. Its specific reactivity and stability under controlled conditions allow researchers to explore new pathways and develop innovative synthetic strategies.
Used in Pharmaceutical Development:
Although not commonly encountered outside of professional or academic contexts, 2-(9H-Fluoren-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane may have potential applications in the development of pharmaceutical compounds. Its unique structure could be harnessed to create new drug candidates or improve the synthesis of existing medications, contributing to advancements in healthcare and medicine.

Upstream product

• 30084-90-3 9H-fluorene-2-carbaldehyde 
• 73183-34-3 bis(pinacol)diborane 
• 2523-42-4 2-iodo-9H-fluorene 
• 13261-62-6 N,N-dimethyl-2-aminofluorene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 480424-61-1 fluorene-2-boronic acid 
• 86-73-7 9H-fluorene 
• 13517-10-7 boron triiodide 
• 1133-80-8 2-bromo-9H-fluorene 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 

Downstream Products

• 1621070-12-9 C₆₅H₆₀N₂O₄ 
• 1250-59-5 Bianthryl-(2,2') 

Relevant academic research and scientific papers

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Hydride Transfer Enables the Nickel-Catalyzed ipso-Borylation and Silylation of Aldehydes

Nickel-catalyzed ipso-borylations and silylations of aldehydes are described for the first time. The new functional-group interconversion protocol is characterized by its scalability, functional-group tolerance and wide substrate scope, including examples of late-stage functionalization of complex molecules. The key for the successful reaction outcome is the use of a ketone as a hydride acceptor that intercepts the nickel hydride to undergo a reductive pathway, thus allowing formation of the desired C?B and C?Si bonds.

Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide

Electrophilic C-H borylation of arenes using boron triiodide has been developed. This reaction proceeded smoothly in the absence of additives, and the diiodoboryl group was installed at the most sterically accessible carbon, where the HOMO is localized to a certain extent. Moreover, regioselective multiple borylation of polycyclic aromatic compounds was achieved by using excess boron triiodide. The borylated intermediates were transformed into a variety of arylboron compounds such as arylboronates, boronic acids, and trifluoroborates.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

BORON DIIODIDE COMPOUND, AND BORONIC ACID, BORONIC ESTER AND THE LIKE OBTAINED THEREFROM, AND PRODUCTION METHOD OF THEM

PROBLEM TO BE SOLVED: To provide a method which enables simple production of a boronic acid, a boronic ester compound or the like suitable for production of various compounds. SOLUTION: The problem is solved by a boron diiodide compound represented by the following general formula (Y). (In the formula (Y), Ar is an n-valent heteroaryl ring, aryl ring having 10 or more carbon atoms, or substituted benzene ring, where at least one hydrogen atom in these rings may be substituted; n is an integer from 1 to 6; and at least one hydrogen atom in the compound represented by the formula (Y) may be substituted with deuterium.) COPYRIGHT: (C)2019,JPO&INPIT

Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light

Converting organoboron compounds into the corresponding radicals has broad synthetic applications in organic chemistry. To achieve these transformations, various strong oxidants such as Mn(OAc)3, AgNO3/K2S2O8, and Cu(OAc)2, in stoichiometric amounts are required, proceeding by a single-electron transfer mechanism. Established herein is a distinct strategy for generating both aryl and alkyl radicals from organotrifluoroborates through an SH2 process. This strategy is enabled by using water as the solvent, visible light as the energy input, and diacetyl as the promoter in the absence of any metal catalyst or redox reagent, thereby eliminating metal waste. To demonstrate its synthetic utility, an efficient acetylation to prepare valuable aryl (alkyl) methyl ketones is described and applications to construct C?C, C?I, C?Br, and C?S bonds are also feasible. Experimental evidence suggests that triplet diacetyl serves as the key intermediate in this process.

Preparation method of aryl borate ester and allyl borate ester

The invention discloses a preparation method of aryl borate ester and allyl borate ester. The method comprises the following step: under the catalytic action of pyridine or a derivative thereof, carrying out 1) or 2) to obtain substituted boric acid ester shown as a formula I-1 or a formula I-2: 1) a reaction of a halide, bi-boric acid ester and alkoxide; 2) a reaction of a halide and a bi-boric acid ester-alkoxide complex. The method is an efficient preparation method of the aryl borate ester and the allyl borate ester. In the preparation method provided by the invention, the inexpensive pyridine or the derivative thereof is taken as a catalyst instead of a transition metal catalyst, the reaction conditions are mild, the reaction yield is high, residues of trace transition metal in a boronation product are avoided, and the cost of an aryl and allyl borate ester synthesis reaction is lowered.

Lanthanide chelate for new chromophore structure

The present application discloses novel lanthanide chelate designs (Formula (I) and Formula (III)) having fluorenyl-, fluorenylethynyl, 9H-carbazolyl-, 9H-carbozolylethynyl-, dibenzothiophenyl-, dibenzothiophenylethynyl-, dibenzofuranyl or dibenzofuranylethynyl pyridine chromophores around an emitting lanthanide ion, e.g. an europium ( 111 ) ion. The three-membered ring chromophores exhibit high molar absorptivity and luminescence with lanthanide ions. The application also discloses a detectable molecule comprising a biospecific binding reactant useful in bioaffinity based binding assay, luminescent lanthanide chelating ligands, as well as a solid support conjugated with the chelates.