Visible‐Light Driven Hydrolysis of Benzyl Halides with Water for Preparation of Benzyl Alcohols

Xu, Jianbin; Liu, Na; Zou, Lingling; Cheng, Feixiang; Shen, Xianfu; Li, Teng; Lv, Haiping; Khan, Ruhima; Fan, Baomin

doi:10.1002/ajoc.201800658

Cited by 13 publications

(6 citation statements)

References 47 publications

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“…Upon the addition of BB, partially quaternized P2VP chains are swelled by the surrounding water. Simultaneously, unquaternized, excess BB molecules undergo hydrolysis and reduce the pH value of the aqueous solution. , Once the aqueous solution becomes sufficiently acidic (i.e., below the p K a of P2VP ∼ 4.7), additional protonated pyridinium ions form within the P2VP chains and subsequently uptake additional water. ,, To better understand the correlation between the particle shape changes and the pH of the surrounding medium, we measured the pH values of the particle suspensions (Table S3) and compared them with the corresponding q of P2VP chains and the resulting particle shape. We note that for accurate measurement, the pH values of particle suspensions were measured before the removal of residual surfactants to prevent any loss of free BB molecules.…”

Section: Resultsmentioning

confidence: 99%

Investigating Structural Effects of Quaternizing Additives on Shape Transitions of Block Copolymer Particles

et al. 2022

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Co-assembly of block copolymers (BCPs) and organic/inorganic additives affords the design of various hierarchical nanostructures. In this work, we investigate the shape-changing capabilities of poly(styrene-block-2-vinylpyridine) (PS-b-P2VP) BCP particles upon quaternization with a series of bromoalkyl benzene additives with different alkyl spacer lengths. The bromoalkyl benzene additives exhibit different hydrolyzing and quaternizing behaviors depending on their chemical structures. When benzyl bromide (BB) is used, the PS-b-P2VP BCP particles exhibit dramatic shape transitions from ellipsoids to ellipsoids with swelled discs, swelled buds, and vesicles. These morphological transitions are attributed to the synergistic quaternization and protonation of the P2VP chains via the hydrolysis of BB in aqueous media. Upon increasing the molar ratio of BB to 2VP units, the pH of the surrounding aqueous solutions significantly decreases, and the protonated P2VP domains are swelled by the surrounding water, which eventually results in interfacial instability of the emulsion interface. When the additives contain longer alkyl spacers (e.g., ethyl, butyl, and hexyl), the additives lead to a narrower range of quaternization-dependent particle morphologies due to the absence of the hydrolysis of the additives. However, a broader spectrum of particle shapes is observed for additives with longer alkyl chains, due to their stronger quaternizing capabilities. We carefully investigate the structural effect of the quaternizing additives on the change of pH, degree of quaternization, and interfacial tension to elucidate the mechanism of the additive-driven particle morphology transitions.

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Section: Resultsmentioning

confidence: 99%

Investigating Structural Effects of Quaternizing Additives on Shape Transitions of Block Copolymer Particles

et al. 2022

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“…And as shown in scheme 4, the formation of desired product 4 c was significantly suppressed in the presence of TEMPO and BHT (1.0 equiv), indicating that a radical process might be involved in this reaction (Scheme 3, i). [20] We then conducted the KIE study with mono-deuterated 3 d, where the K H /K D = 2.2 implied the CÀ H bond cleavage in the ratedetermining step (Scheme 4, ii).…”

Section: Resultsmentioning

confidence: 99%

Catalyst/Additive Free Oxidation of Benzyl Bromides to Benzaldehydes

Aman

Chen

et al. 2020

ChemistrySelect

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“…In all the aforementioned examples (Table ), the reactions afforded the desired products in almost quantitative yields (95–99%) without the detection of the corresponding benzyl alcohols (TLC, GC–MS). This might be attributed to the fact that such reaction required strong bases or photocatalysts[41a] and benzyl halides are attacked by the azide nucleophile (good nucleophile) more faster than their attack by water (weak nucleophile) [10,21,22a,30a,41]…”

Section: Resultsmentioning

confidence: 99%

Water as a solvent for Ru‐catalyzed click reaction: Highly efficient recyclable catalytic system for triazolocoumarins synthesis

Arafa

Nayl

2019

Applied Organom Chemis

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A new family of Ru (III) complexes has been synthesized, characterized and their catalytic performance has been tested for alkyne–azide cycloaddition (AAC) in water under ultrasonic irradiation conditions. These complexes are found to be effective heterogeneous catalysts for the regioselective synthesis of 1,4‐disubstituted‐1,2,3‐triazoles giving access to these products in excellent yields. The catalyst system is equally active for one‐pot multi‐component protocol of the AAC reactions. Also, successive sequencing of Huisgen reaction with Knoevenagel condensation reaction results in the effective assembly of a diversified hitherto unreported 1,2,3‐triazolyl coumarin frameworks. In present strategy, the catalyst could be easily isolated by simple filtration and reused up to eight consecutive cycles without significant drop in the reaction yields. During the leaching experiment, there is no leaching amount of the catalyst was detected, suggesting true heterogeneity in the catalytic system. The results of gram‐scale reaction and green metrics calculations also confirmed the sustainability and industrial applicability of the current catalytic protocol.

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Visible‐Light Driven Hydrolysis of Benzyl Halides with Water for Preparation of Benzyl Alcohols

Abstract: Visible-light-mediated hydrolysis of benzyl halides has been achieved that is efficiently catalyzed by metal-free catalyst rhodamine B. Benzyl bromides and chlorides can smoothly react with water to prepare a series of benzyl alcohol compounds in good yields.[a] Dr.

Cited by 13 publications

References 47 publications

Investigating Structural Effects of Quaternizing Additives on Shape Transitions of Block Copolymer Particles

Investigating Structural Effects of Quaternizing Additives on Shape Transitions of Block Copolymer Particles

Catalyst/Additive Free Oxidation of Benzyl Bromides to Benzaldehydes

Water as a solvent for Ru‐catalyzed click reaction: Highly efficient recyclable catalytic system for triazolocoumarins synthesis

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