99810-76-1

Usage

Uses

Used in Pharmaceutical Industry:
Tert-Butylboronic acid pinacol ester is used as a reagent in the synthesis of biaryl compounds for their application in the development of pharmaceuticals. The formation of these compounds is crucial for the creation of new drugs and the improvement of existing ones.
Used in Material Science Research:
In the field of material science, tert-Butylboronic acid pinacol ester is utilized as a precursor in the synthesis of biaryl compounds, which are integral to the development of advanced materials with specific properties.
Used in Organic Synthesis:
Tert-Butylboronic acid pinacol ester is employed as a reagent for the formation of carbon-carbon bonds in various organic synthesis processes, facilitating the creation of complex organic molecules and contributing to the advancement of synthetic chemistry.
Used in the Development of New Synthetic Methods:
tert-Butylboronic acid pinacol ester is used as a key component in the research and development of innovative synthetic methods, enhancing the efficiency and scope of chemical reactions in the synthesis of complex organic molecules.

InChI:InChI=1/C10H21BO2/c1-8(2,3)11-12-9(4,5)10(6,7)13-11/h1-7H3

Upstream product

• 2259-30-5 tert-butylmagnesium bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 507-19-7 t-butyl bromide 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 46275-90-5 N-methyl-2-(1,1-dimethylethyl)indole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 768-56-9 4-Phenylbut-1-ene 
• 184370-59-0 (E)-1-iodo-4-phenyl-1-butene 
• 830345-63-6 (Z)-(5,5-dimethylhex-3-en-1-yl)benzene 
• 97571-08-9 2-(3,3-dimethyl-1-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 86253-12-5 t-butylboronic acid 

Relevant academic research and scientific papers

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

A Zinc Catalyzed C(sp3)?C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates

The Suzuki–Miyaura (SM) reaction is one of the most important methods for C?C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.

Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group

Iodine reacts with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin), under ambient reaction conditions in THF, to form the iodoalkylborate species 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4-IboxBpin). Apparently, one-half equivalent of I2 reacts with HBpin to form IBpin in pentanes, which in turn cleaves THF to form the 4-IboxBpin. Alkyl and aryl Grignard reagents, prepared under Barbier conditions, then react with 4-IboxBpin to form the corresponding alkyl and aryl pinacolboronates while reforming and liberating THF as the leaving group.

Highly nucleophilic dipropanolamine chelated boron reagents for aryl-transmetallation to iron complexes

New aryl- and heteroarylboronate esters chelated by dipropanolamine are synthesised directly from boronic acids. The corresponding anionic borates are readily accessible by deprotonation and demonstrate an increase in hydrocarbyl nucleophilicity in comparison to other common borates. The new borates proved competent for magnesium or zinc additive-free, direct boron-to-iron hydrocarbyl transmetallations with well-defined iron(ii) (pre)catalysts. The application of the new borate reagents in representative Csp2-Csp3 cross-coupling led to almost exclusive homocoupling unless coupling is performed in the presence of a zinc additive.

SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS

Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.

Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters

Grignard reagents (aliphatic, aromatic, heteroaromatic, vinyl, or allylic) react with 1 equiv of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, PinBH) at ambient temperature in tetrahydrofuran (THF) to afford the corresponding pinacolboronates. The initially formed dialkoxy alkylborohydride intermediate quickly eliminates hydridomagnesium bromide (HMgBr) and affords the product boronic ester in very good yield. Hydridomagnesium bromide (HMgBr) in turn disproportionates to a 1:1 mixture of magnesium hydride (MgH2) and magnesium bromide (MgBr2) on addition of pentane to the reaction mixture. DFT calculations (Gaussian09) at the B3LYP/6-31G(d) level of theory show that disproportionation of HMgBr to MgH2 and MgBr2 is viable in the coordinating ethereal solvents. This reaction also can be carried out under Barbier conditions, where the neat PinBH is added to the flask prior to the in situ formation of Grignard reagent from the corresponding organic halide and magnesium metal. Pinacolboronic ester synthesis under Barbier conditions does not give Wurtz coupling side products from reactive halides, such as benzylic and allylic halides. The reaction between PinBH and various Grignard reagents is an efficient, mild, and general method for the synthesis of pinacolboronates.