67562-19-0

Usage

Uses

Used in Organic Synthesis:
n-Propyl boronic acid pinacol is used as a building block for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its pinacol functionality provides stability and solubility, making it a useful reagent in various synthetic applications.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
n-Propyl boronic acid pinacol is used as a reagent in Suzuki-Miyaura cross-coupling reactions to introduce the n-propyl group into organic molecules. This reaction is a widely used method for the formation of carbon-carbon bonds, allowing for the synthesis of a wide range of organic compounds.
It should be noted that n-Propyl boronic acid pinacol should be handled and stored with care due to its potential reactivity and toxicity.

Upstream product

• 1116-61-6 tripropylborane 
• 67-63-0 isopropyl alcohol 
• 67-64-1 acetone 
• 590-13-6 (Z)-1-propenyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1360649-09-7 2-(1-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1333-74-0 hydrogen 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 10294-33-4 boron tribromide 
• 75-19-4 cyclopropane 
• 133165-98-7 1-methyl-2-n-propyl-1H-indole 
• 73183-34-3 bis(pinacol)diborane 
• 107-08-4 1-iodo-propane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 105-30-6 (S)-2-methyl-1-pentanol 

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

One-pot synthesis of Ag-Cu-Cu2O/C nanocomposites derived from a metal-organic framework as a photocatalyst for borylation of aryl halide

Mixed metal-metal oxide/C (Ag-Cu-Cu2O/C) nanocomposites were synthesized by the heat treatment of a metal-organic framework under a N2 flow using the one-pot synthesis method. The as-prepared nanocomposites were characterized using a range of techniques,

Photo-induced radical borylation of hemiacetals via C–C bond cleavage

In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed.

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

Study of chemoselective asymmetric hydrogenation of (1-bromo-1-alkenyl) boronic esters with iridium-P?N complexes

In this paper we report the first chemoselective asymmetric hydrogenation of (1-bromo-1-alkenyl)boronic esters, which constitutes a new route to (α-bromoalkyl)boronic esters. The study demonstrates that excellent chemoselectivities along with full conversions can be obtained for hydrogenation of alkyl substituted derivatives with iridium-P?N complexes. Moreover, acyclic alkyl derivatives afford (α-bromoalkyl)boronic esters in good enantioselectivities ranging from 64 to 73% ee. A cyclic alkyl derivative was obtained only in a nearly racemic form. The (1-bromo-1-alkenyl)boronic esters appear to be less reactive towards homogenous hydrogenation conditions than their chloro analogues as demonstrated by the higher catalyst loadings required to achieve full conversions for alkyl derivatives and lower conversions observed for the aryl substituted derivatives.

A practical synthetic approach to chiral (α-chloroalkyl)boronic esters via iridium-catalyzed chemoselective hydrogenation of chloro-substituted alkenyl boronates

Chiral (α-chloroalkyl)boronic esters are obtained by homogeneous asymmetric iridium-catalyzed chemoselective hydrogenation of (1-chloro-1-alkenyl)boronic esters. P,N-Iridium catalysis provides low level of dehalogenation during the hydrogenation, while th

Replacing conventional carbon nucleophiles with electrophiles: Nickel-catalyzed reductive alkylation of aryl bromides and chlorides

A general method is presented for the synthesis of alkylated arenes by the chemoselective combination of two electrophilic carbons. Under the optimized conditions, a variety of aryl and vinyl bromides are reductively coupled with alkyl bromides in high yields. Under similar conditions, activated aryl chlorides can also be coupled with bromoalkanes. The protocols are highly functional-group tolerant (-OH, -NHTs, -OAc, -OTs, -OTf, -COMe, -NHBoc, -NHCbz, -CN, -SO2Me), and the reactions are assembled on the benchtop with no special precautions to exclude air or moisture. The reaction displays different chemoselectivity than conventional cross-coupling reactions, such as the Suzuki-Miyaura, Stille, and Hiyama-Denmark reactions. Substrates bearing both an electrophilic and nucleophilic carbon result in selective coupling at the electrophilic carbon (R-X) and no reaction at the nucleophilic carbon (R-[M]) for organoboron (-Bpin), organotin (-SnMe3), and organosilicon (-SiMe2OH) containing organic halides (X-R-[M]). A Hammett study showed a linear correlation of σ and σ(-) parameters with the relative rate of reaction of substituted aryl bromides with bromoalkanes. The small ρ values for these correlations (1.2-1.7) indicate that oxidative addition of the bromoarene is not the turnover-frequency determining step. The rate of reaction has a positive dependence on the concentration of alkyl bromide and catalyst, no dependence upon the amount of zinc (reducing agent), and an inverse dependence upon aryl halide concentration. These results and studies with an organic reductant (TDAE) argue against the intermediacy of organozinc reagents.

Iridium-catalyzed chemoselective and enantioselective hydrogenation of (1-Chloro-1-Alkenyl) boronic esters

Persistent chlorine: Hydrogenation of borolane-substituted vinylic chlorides catalyzed by Ir-P N complexes greatly preserved the chlorine substituent on the hydrogenated product, with only 3-19 % of dechlorinated byproducts present after hydrogenation. Th

Combining high pressure and catalysis: Pinacol- or catecholborane hydroboration of functionalized olefins

The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from the undesired β-bromoboronate regioisomer. By contrast, catecholborane (CBH) affords mainly the expected α-bromoboronate at atmospheric pressure. With dibenzylallylamine, PBH yields a mixture of the two possible regioisomers (β- and γ-aminoboronates), whatever the pressure, while CBH affords selectively the expected γ-isomer in good yields under atmospheric thermal conditions. For 2,3-dihydrofuran, only PBH gives an efficient access, in THF, to a mixture of the corresponding α- and β-regioisomers when combining the effects of 0.5% Wilkinson's catalyst and high pressure. The Royal Society of Chemistry 2000.