329685-40-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-1-propylboronic acid pinacol ester, 97% is used as a key intermediate in the synthesis of various pharmaceutical drugs due to its functional group compatibility and high chemical stability. Its ability to participate in the Suzuki reaction, a type of coupling reaction, makes it advantageous for creating complex molecular structures that are often required in drug development.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3-Phenyl-1-propylboronic acid pinacol ester, 97% serves as a valuable reagent for the synthesis of complex organic compounds. Its stability and ease of handling make it an ideal choice for researchers working on the development of new chemical entities and the exploration of novel synthetic pathways.

Upstream product

• 766-90-5 cis-1-phenyl-1-propylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 104-53-0 3-phenyl-propionaldehyde 
• 73183-34-3 bis(pinacol)diborane 
• 1379610-52-2 4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane 
• 61124-61-6 3-phenylpropanal p-tosylhydrazone 
• 108-86-1 bromobenzene 
• 124215-44-7 2-(3-Bromopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 300-57-2 allylbenzene 
• 103-65-1 phenylpropane 
• 116199-39-4 4-phenylbutan-2-yl 4-methylbenzene-1-sulfonate 
• 1448901-30-1 (1,3-dimethyl-1H-imidazol-3-ium-2-yl)(1-methoxy-1-oxo-3-phenylpropan-2-yl)dihydroborate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 

Downstream Products

• 113138-08-2 1-(4-(3-phenylpropyl)phenyl)ethan-1-one 
• 36329-85-8 (3-phenylpropyl)boronic acid 
• 104315-86-8 1-trifluoromethyl-3-phenylpropane 
• 63635-59-6 1-(p-Chlorophenyl)-3-phenylpropane 
• 879893-72-8 2-methoxy-5-(3-phenylprop-1-yl)pyridine 
• 1101197-19-6 2-phenyl-6-(3-phenylpropyl)pyridine 

Relevant academic research and scientific papers

Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of di

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.

Hydroboration of Terminal Alkenes and trans-1,2-Diboration of Terminal Alkynes Catalyzed by a Manganese(I) Alkyl Complex

A MnI-catalyzed hydroboration of terminal alkenes and a 1,2-diboration of terminal alkynes with pinacolborane (HBPin) is described. For alkenes, anti-Markovnikov hydroboration takes place; for alkynes the reaction proceeds with excellent trans-1,2-selectivity. The most active pre-catalyst is bench-stable alkyl bisphosphine MnI complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn–alkyl bond to yield an acyl intermediate, which undergoes B?H bond cleavage of HBPin (for alkenes) and rapid C?H bond cleavage (for alkynes), forming the active MnI boryl and acetylide catalysts [Mn(dippe)(CO)2(BPin)] and [Mn(dippe)(CO)2(C≡CR)], respectively. A broad variety of aromatic and aliphatic alkenes and alkynes was efficiently and selectively borylated. Mechanistic insights are provided based on experimental data and DFT calculations revealing that an acceptorless reaction is operating involving dihydrogen release.

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

In the past decade, the use of earth-abundant metals in homogeneous catalysis has flourished. In particular, metals such as cobalt and iron have been used extensively in reductive transformations including hydrogenation, hydroboration, and hydrosilylation

Synthesis and Catalytic Reactivity of Cobalt Pincer Nitrosyl Hydride Complexes

The synthesis, characterization, and catalytic activity of low-spin {CoNO}8 pincer complexes of the type [Co(PCP)(NO)(H)] are described. These compounds are obtained either by reacting [Co(PCP)(κ2-BH4)] with NO and Et3N or, alternatively, by reacting [Co(

Highly Selective Hydroboration of Terminal Alkenes Catalyzed by a Cobalt Pincer Complex Featuring a Central Reactive N-Heterocyclic Phosphido Fragment

The application of a cobalt pincer complex, (PPClP)CoCl2, as a precatalyst for the hydroboration of terminal alkenes with pinacolborane (HBPin) is described. The reactions proceed rapidly under mild conditions (room temperature, 30 min) with low catalyst

Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**

An unprecedented and general hydroboration of alkenes with BX3 (X=Br, Cl) as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene polymerizat

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.