Pd-Catalyzed, Highly Selective C(sp2)-Br Bond Coupling Reactions of o-(or m-, or p-) Chloromethyl Bromobenzene with Arylboronic Acids

Pei, Ming-Ming; Liu, Ping; Liu, Yan; Lv, Xin-Ming; Ma, Xinbin; Dai, Bin

doi:10.3390/molecules23020433

Cited by 5 publications

(3 citation statements)

References 44 publications

(38 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Note: trimethylphosphine is a pyrophoric compound and should be handled carefully by appropriately trained individuals using inert atmosphere techniques. To prepare comonomer f , 4-chloromethyl-4′-vinyl-1,1′-biphenyl ( f′ ) was first synthesized based on a Suzuki-Miyaura coupling procedure reported by Pei and co-workers . The Suzuki-Miyaura product f′ underwent a nucleophilic substitution reaction with trimethylphosphine in anhydrous toluene as described above, yielding comonomer f .…”

Section: Methodsmentioning

confidence: 99%

“…A general nucleophilic substitution was performed as To prepare comonomer f, 4-chloromethyl-4′-vinyl-1,1′-biphenyl (f′) was first synthesized based on a Suzuki-Miyaura coupling procedure reported by Pei and co-workers. 38 The Suzuki-Miyaura product f′ underwent a nucleophilic substitution reaction with trimethylphosphine in anhydrous toluene as described above, yielding comonomer f. Detailed synthetic procedures and spectroscopic characterization of f′ and f are provided in Section A of the Supporting Information. Synthesis of StyDex Polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Structural Features of Styrene-Functionalized Cyclodextrin Polymers That Promote the Adsorption of Perfluoroalkyl Acids in Water

Lin,

Wang,

Dyakiv

et al. 2024

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Cross-linked β-cyclodextrin (β-CD) polymers are promising adsorbents for the removal of per-and polyfluoroalkyl substances (PFAS) from contaminated water sources, including contaminated groundwater, drinking water, and wastewater. We previously reported porous, styrene-functionalized β-cyclodextrin (StyDex) polymers derived from radical polymerization with vinyl comonomers. Because of the versatility of these polymerizations, StyDex polymer compositions are tunable, which facilitates efforts to establish structure−adsorption relationships and to discover improved materials. Here, we evaluate the material properties and PFAS adsorption of 20 StyDex derivatives with varied comonomer structure and loading, regiochemistry of styrene placement on the CD monomer, and CD size. A StyDex polymer containing N,N′dimethylbutyl ammonium ions exhibited the most effective PFAS adsorption in batch experiments. Furthermore, a StyDex polymer containing β-CD exhibited size-selective host−guest interactions with perfluoroalkyl acids (PFAAs) and neutral contaminants in aqueous electrolyte when compared to similar polymers containing either α-CD or γ-CD. Polymers based on β-CD monomers with an average of seven styrene groups randomly positioned over the 21 available hydroxyl groups performed similarly to those based on a β-CD monomer functionalized regiospecifically at each of the seven 6′ positions. The former β-CD monomer is prepared in a single step from unmodified β-CD, so the ability to use it without compromising performance demonstrates promise for developing economically competitive adsorbents. These results offered important insights into structure−adsorption properties of StyDex polymers and will inform the design of improved StyDex formulations.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Structural Features of Styrene-Functionalized Cyclodextrin Polymers That Promote the Adsorption of Perfluoroalkyl Acids in Water

Lin,

Wang,

Dyakiv

et al. 2024

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…In the second step, bromine at para position is used for the Suzuki C–C coupling reaction, as shown in Scheme . It is also used as an intermediate in other N -alkylations, S -alkylations, and most importantly in C–C cross-coupling reactions. − …”

Section: Introductionmentioning

confidence: 99%

Continuous Synthesis and Separation of p-Bromobenzyl Bromide Using Atom-Efficient Bromination of p-Bromotoluene without Any Organic Effluent: Potential for Green Industrial Practice

Sancheti

Yadav

2021

Org. Process Res. Dev.

View full text Add to dashboard Cite

This work focuses on the bromination of p-bromotoluene (PBT) using different brominating agents such as liquid Br2, NaBr–NaBrO3, NaBr–NaBrO3–NaCl, NaBr–H2O2, and HBr–H2O2. NaBr–NaBrO3–NaCl is an eco-friendly brominating agent obtained from a bromine recovery plant. Both NaBr–NaBrO3 and NaBr–NaBrO3–NaCl were found to be nonhazardous and efficient brominating agents. Pure NaBr–NaBrO3 resulted in the best PBT conversion with 79.7% Br atom efficiency in water and 98.2% average Br atom efficiency using dichloroethane as a solvent. Dichloroethane is de facto no longer used in the US and Europe and is not eco-friendly; the process with water as a solvent is the best. The substrate to active bromine molar ratio of 3:1 was found to be sufficient to get the maximum selectivity of p-bromobenzyl bromide (PBBB). The low-temperature crystallization method was used for separation cum purification of the product. Unreacted PBT was recycled along with the dibromo byproduct obtained. The dibromo product, which was built up gradually in the reaction mixture over 10 successive batches, was converted back into PBBB/PBT through NaBH4 treatment of the mother liquor. This continuous process is highly sustainable and produces zero organic waste, making it potentially attractive toward green industrial implementation.

show abstract

Pd‐Catalyzed Chemoselective Suzuki‐Miyaura Reactions of 1‐Bromo‐4‐(halomethyl)naphthalene

Pei

Liu

et al. 2018

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

A Pd‐catalyzed chemoselective Suzuki‐Miyaura reaction of 1‐bromo‐4‐(halomethyl)naphthalene and arylboronic acids for the formation of C(sp3)–C(sp2) bond via highly selective C(sp3)‐X bond cleavage is disclosed, which enables the general synthesis of functionalized 1‐benzyl‐4‐bromonaphthalene compounds in good yields under mild conditions. Moreover, the 1‐benzyl‐4‐bromonaphthalene was also obtained on a multi‐gram scale, and further to prepare more complex target molecules through the related chemical transformation.

show abstract

Pd-Catalyzed, Highly Selective C(sp2)-Br Bond Coupling Reactions of o-(or m-, or p-) Chloromethyl Bromobenzene with Arylboronic Acids

Cited by 5 publications

References 44 publications

Structural Features of Styrene-Functionalized Cyclodextrin Polymers That Promote the Adsorption of Perfluoroalkyl Acids in Water

Structural Features of Styrene-Functionalized Cyclodextrin Polymers That Promote the Adsorption of Perfluoroalkyl Acids in Water

Continuous Synthesis and Separation of p-Bromobenzyl Bromide Using Atom-Efficient Bromination of p-Bromotoluene without Any Organic Effluent: Potential for Green Industrial Practice

Pd‐Catalyzed Chemoselective Suzuki‐Miyaura Reactions of 1‐Bromo‐4‐(halomethyl)naphthalene

Contact Info

Product

Resources

About