1190375-91-7

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 75927-49-0 pinacol vinylboronate 
• 35283-06-8 3-(4-(dimethylamino)phenyl)propiolic acid 
• 73183-34-3 bis(pinacol)diborane 
• 2039-80-7 N,N-dimethy-4-vinylaniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 
• 2124-31-4 4'-dimethylaminoacetophenone 
• 92146-68-4 4-(2-methoxyethenyl)-N,N-dimethylaniline 

Downstream Products

• 1266052-57-6 C₁₀H₁₂IN 

Relevant academic research and scientific papers

Lithium compounds as single site catalysts for hydroboration of alkenes and alkynes

The hydroboration of alkenes and alkynes using easily accessible lithium compounds [2,6-di-tert-butyl phenolatelithium (1a) and 1,1′ dilithioferrocene (1b)] has been achieved with good yields, high functional group tolerance and excellent chemoselectivity

Copper-catalyzed decarboxylative hydroboration: Synthesis of vinyl boronic esters

Vinyl boronic esters were synthesized from aryl alkynyl carboxylic acids and bis(pinacolato)diboron using a copper-catalyzed decarboxylative reaction. The reaction was conducted with CuI (10 mol%), bis-[2-(diphenylphosphino)phenyl]ether(20 mol%), and LiOM

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.

Pluripotent Features of Doubly Thiophene-Fused Benzodiphospholes as Organic Functional Materials

Linear ladder-type π-conjugated molecules have attracted much interest because of their intriguing physicochemical properties. To modulate their electronic structures, an effective strategy is to incorporate main-group elements into ladder-type π-conjugated molecules. In line with this strategy, a variety of ladder-type π-conjugated molecules with main-group elements have been synthesized to explore their potential utility as organic functional materials. In this context, phosphole-based π-conjugated molecules are highly attractive, owing to their unique optical and electrochemical properties, which arise from the phosphorus atom. Herein, the synthesis and physicochemical properties of doubly thiophene-fused benzodiphospholes, as a new class of phosphole-based ladder-type π-conjugated molecule, are reported. Systematic investigations into the physicochemical properties of doubly thiophene-fused benzodiphospholes revealed their pluripotent features: intense near-infrared fluorescence, excellent two-photon absorption property, and remarkably high electron-transporting ability. This study demonstrates the potential utility of doubly thiophene-fused benzodiphospholes as organic functional materials for biological imaging, nonlinear optics, organic transistors, and organic photovoltaics.

Two-Photon Sensitive Coumarinyl Photoremovable Protecting Groups with Rigid Electron-Rich Cycles Obtained by Domino Reactions Initiated by a 5- exo-Dig Cyclocarbopalladation

We herein report the design, synthesis, and photophysical characterization of extended and rigid coumarinyl derivatives showing large two-photon sensitivities (δaφu ≤ 125 GM) at 740 and 800 nm. To efficiently synthesize these complex photoremovable protecting groups (PPGs), we used step-economic domino reactions. Moreover, those new coumarinyl PPGs display unique bathochromic shifts (≤100 nm) of the uncaging subproducts as a result of the formation of a more conjugated fulvene moiety.

Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point

Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.

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.

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage

A new protocol has been developed for the borylation of conjugated alkenyl methyl ethers using B2Pin2 via C-O bond cleavage catalyzed by Ni(II). In this cross-coupling reaction, both E/Z isomers of alkenyl ethers are converted into (E)-alkenyl boronic esters with good reactivity. This transformation exhibits high chemoselectivity in the presence of competitive C-O bonds such as aryl ether, ester, amide, and thioether groups, thus providing a new method for the construction of various alkenyl boronates.

Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes

A simple and rapid protocol for the anti-Markovnikov hydroboration of alkynes assisted by microwave irradiation has been developed. Pinacolborane smoothly reacts with terminal alkynes to obtain (E)-alkenyl boronates in good yields and short reactions times in the absence of solvent. Further transformations on the carbon-boron bond of the adducts can be sequentially achieved without the need of purifying the alkenyl boronates.