Facile and selective deprotection of PMB ethers and esters using oxalyl chloride

Ilangovan, Andivelu; Anandhan, Karnambaram; Kaushik, M. P.

doi:10.1016/j.tetlet.2015.01.061

Cited by 8 publications

(7 citation statements)

References 37 publications

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“…The synthesis was carried out according to the reaction of benzyl chloride with phenol . In a typical procedure, chloromethylated polystyrene beads were washed with ethanol and water under ultrasonic conditions several times and dried in an oven at 333 K overnight before use.…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis was carried out according to the reaction of benzyl chloride with phenol. 41 In a typical procedure, chloromethylated polystyrene beads were washed with ethanol and water under ultrasonic conditions several times and dried in an oven at 333 K overnight before use. Dried chloromethylated polystyrene beads (1.0 g, chlorine: 5 mmol) were swollen in DMF (10 mL, dried with calcium hydride before use) at room temperature for 12 h, followed by the addition of boronic acid (7.5 mmol) and base (5 mmol (80, 100 or 140 ∘ C) for 24 h. After being cooled to room temperature, the resins were washed with ethanol and water under ultrasonic conditions several times to remove the residual solvent and boronic acid, and dried in an air dry oven at 323 K for 12 h. The synthesized resins were named as BA-base-t.…”

Section: Preparation Of Boronic Acid Functionalized Resinmentioning

confidence: 99%

Section: Preparation Of Boronic Acid Functionalized Resinmentioning

confidence: 99%

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Efficient and selective adsorption of small polyols by boronic acid functionalized polystyrene adsorbent

Jia

Sun

Yin

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND The separation of polyols from fermentation broth remains a challenge due to their high boiling points and strong hydrophilicity, however, they show pH‐dependent reversible interaction with boronic acid, which makes it a perfect moiety for the construction of functional adsorbents for polyols enrichment. RESULTS Boronic acid functionalized polystyrene adsorbents were successfully synthesized by loading N‐ or O‐substituted phenylboronic acid into chloromethylated polystyrene resin. Aminophenyl boronic acid modified resin exhibits the best adsorption capacities, 0.34 mmol g−1 for glycerol and 0.27 mmol g−1 for 1,2,4‐butanetriol in aqueous solution, whereas the adsorption capacities of most commercial resins are below 0.07 mmol g−1. The adsorption capacity increased with increasing alkalinity and the boronic ester dissociates when subjected to acidic conditions. The reversible interaction facilitates regeneration of the adsorbent, and the resin displayed good adsorption stability during six reuses. CONCLUSION The functional resin displays great adsorption advantage over commercial resins and adsorptive preference for 1,2‐ and 1,3‐polyols rather than 1,4‐polyol in double‐adsorbate systems, distinctive from commercial resin whose adsorption capacity is mainly determined by the hydrophilicity of the adsorbate. Thus, boronic acid functionalized polystyrene adsorbent is a potential adsorbent for polyol enrichment from fermentation. © 2018 Society of Chemical Industry

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Section: Methodsmentioning

confidence: 99%

Section: Preparation Of Boronic Acid Functionalized Resinmentioning

confidence: 99%

Section: Preparation Of Boronic Acid Functionalized Resinmentioning

confidence: 99%

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Efficient and selective adsorption of small polyols by boronic acid functionalized polystyrene adsorbent

Jia

Sun

Yin

et al. 2019

J of Chemical Tech & Biotech

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“…Change of reagent to SOCl 2 lead to a decrease in the yields of the products. The salient features of the methods included short reaction time, mild reaction conditions, easy isolation of the product and broad substrate scope …”

Section: Miscellaneousmentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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Oxalyl chloride, (COCl)2, as an inexpensive commercially available chemical is one of the most versatile applicable organic reagents in chemical transformations. It is also employed extensively in various chemical industries. It is employed in various chemical transformations such as chlorination, oxidation, reduction, dehydration, decarboxylation, and formylation reactions as well as ring cleavage of epoxides. During the past decades, numerous procedures using (COCl)2 as reagent have been developed and published. However, its importance has largely been overlooked by the absence of a comprehensive review in chemical literature dealing with its application in organic transformations and its utilization in the chemical industry. This Review aims to provide an overview for the applications of oxalyl chloride in organic synthesis, including its physical properties, synthesis, as well as its unique roles as the reagent in organic reactions, covering the literature over the past 103 years (from 1916 to date).

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“…Spectral analysis is consistent with previously published data. 31 Yield: 160 mg, 70% yield. Physical State:.…”

Section: S32mentioning

confidence: 99%

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

Escobar¹,

Johannes

2019

Preprint

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<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

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Facile and selective deprotection of PMB ethers and esters using oxalyl chloride

Cited by 8 publications

References 37 publications

Efficient and selective adsorption of small polyols by boronic acid functionalized polystyrene adsorbent

Efficient and selective adsorption of small polyols by boronic acid functionalized polystyrene adsorbent

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

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