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Usage

Uses

Used in Pharmaceutical Research and Development:
2-(3-chlorobenzyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane serves as a crucial reagent in the synthesis of complex organic molecules, which are often the foundation for the development of new pharmaceuticals. Its ability to facilitate carbon-carbon bond formation is particularly beneficial in creating molecules with specific therapeutic properties.
Used in Agrochemical Research and Development:
In the agrochemical industry, 2-(3-chlorobenzyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is utilized for the synthesis of compounds with pesticidal or herbicidal properties. Its role in cross-coupling reactions aids in the creation of new molecules that can be more effective and selective in controlling pests and weeds.
Used in Organic Synthesis:
2-(3-chlorobenzyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is employed as a reagent in various organic synthesis processes, where its electron-withdrawing nature and stability contribute to the successful formation of desired products. Its high reactivity and selectivity make it a popular choice for creating complex organic molecules with specific structural features.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
2-(3-chlorobenzyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is particularly useful in Suzuki-Miyaura cross-coupling reactions, a widely used method for the formation of carbon-carbon bonds. Its strong electron-withdrawing properties and stability make it an effective participant in these reactions, leading to the synthesis of a variety of organic compounds with potential applications in various fields.

Upstream product

• 2039-85-2 3-Chlorostyrene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 135145-34-5 (S)-1-(m-chlorophenyl)ethanol 
• 120121-01-9 (R)-1-(3-chlorophenyl)-ethanol 

Relevant academic research and scientific papers

Erratum: Markovnikov-selective hydroboration of olefins catalyzed by a copper N-heterocyclic carbene complex (Organometallics (2019) 38:17 (3322-3326) DOI: 10.1021/acs.organomet.9b00394)

It has come to our attention that some of the products listed in Table 2 of the article and in eq 1 have the incorrect stereochemistry. The reactions of alkynes with HBpin give the linear E-olefin products, not the branched products as were shown. 1H NMR spectra clearly show two doublets with a large J (18 Hz) for the trans-hydrogens of the alkene product. A DEPT-135 spectrum also confirms that CH and not CH2 is present. Corrected eq 1, Table 2, TOC graphic are shown. Note that the alkene addition products are correctly assigned as branched, displaying a doublet and a quartet for the methyl and methane groups, respectively. NMR spectra for all products are included in the revised Supporting Information. We thank Prof. Jaesook Yun for pointing out this error, as her group has worked on related copper borylations for many years.

Palladium-catalyzed regioselective hydroboration of aryl alkenes with B2pin2

A palladium(ii)-catalyzed hydroboration of aryl alkenes with stable and easy-to-handle (pinacolato)diboron (B2pin2) under mild conditions has been developed. Acetic acid acted as the solvent and the hydrogen source, which has been identified by deuterium experiments. Notably, isomerization-hydroboration of allyl benzene derivatives was observed. As a result, a series of benzyl boronic esters were obtained in moderate to excellent yields with exclusive regioselectivity.

Iron-Catalyzed, Markovnikov-Selective Hydroboration of Styrenes

A highly Markovnikov-selective, iron-catalyzed hydroboration of styrenes is reported using available oxazolinylphenyl picolinamide as the ligand to afford the branched hydroboration products with up to >50/1 b/l. This reaction is operationally simple and

DMAP-accelerated rhodium(I) chloride catalyzed hydroboration of vinylarenes

Regioselective hydroboration of vinylarenes catalyzed by a Rh(I)-DPPB complex proceeded rapidly when DMAP was used as an additive. The catalyst loading could be reduced to 0.4 mol% Rh(I) to furnish the desired products in good to excellent yield with high