1415236-89-3

Upstream product

• 71813-50-8 1-bromo-2-(but-3-enyl)benzene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 24892-64-6 1-(but-3-en-1-yl)-2-iodobenzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

A new transition-metal-frec borylation of aryl and vinyl halides using l,l-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemo-selectivity and functional group compatibility, thus offering a rare example of a transition-metal-frec borylation protocol. Experimental and theoretical studies have becn performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct betwecn organohalides and α-borylcarbanion, generated in situ from the reaction of l,l-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions.

Efficient synthesis of aryl boronates via zinc-catalyzed cross-coupling of alkoxy diboron reagents with aryl halides at room temperature

A zinc(II)/NHC system catalyzes the borylation of aryl halides with diboron (4) reagents in the presence of KOMe at rt. This transformation can be applied to a broad range of substrates with high functional group compatibility. Radical scavenger experiments do not support a radical-mediated process.

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.

An organic boron compound

PROBLEM TO BE SOLVED: To provide a production method of an arylboronic acid ester with a wide range of application substrate, using no heavy metal.SOLUTION: An organic halogen compound represented by the general formula R-X (where, X is Br or I; R is a C1 to 20 alkyl group, a C6 to 14 aryl group, a heterocyclic group comprising 1 to 3 hetero atoms selected from N, O and S, or the like) and a compound represented by the general formula (VI) are reacted in the presence of sodium alkoxide or potassium alkoxide for substitution of a substituted Si moiety and the R moiety to obtain arylboronic acid ester. (In the formula, three Rare each independently a C1 to 6 alkyl group or a C6 to 10 aryl group; and four Reach independently a C1 to 3 alkyl group.)

Metal-Free Radical Borylation of Alkyl and Aryl Iodides

A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed.

Zinc-Catalyzed Dual C-X and C-H Borylation of Aryl Halides

A zinc-catalyzed combined C-X and C-H borylation of aryl halides using B2pin2 (pin=OCMe2CMe2O) to produce the corresponding 1,2-diborylarenes under mild conditions was developed. Catalytic C-H bond activation occurs ortho to the halide groups if such a site is available or meta to the halide if the ortho position is already substituted. This method thus represents a novel use of a groupXII catalyst for C-H borylation. This transformation does not proceed via a free aryne intermediate, but a radical process seems to be involved. Two B or not two B: A novel catalytic system based on a ZnII-dtbpy precursor was developed for the preparation of 1,2-diborylarenes. This method represents a new type of catalytic process for diborylation of aryl halides via both C-X and C-H activation.

Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems

An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.