A thermo-regulated highly regioselective mono and dihalogenations of phenols and anilines in water employing new Lewis base adducts (LBAs) [DBUBr]+Br− and [DBUI]+I− as green reagents: a simple approach

Gavinolla, Vijayalaxmi; Thangalipalli, Swathi; Bandalla, Siddarama Goud; Panduga, Ramaraju; Neella, Chandra Kiran

doi:10.1039/d3nj03370h

New J. Chem.

2023

DOI: 10.1039/d3nj03370h

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A thermo-regulated highly regioselective mono and dihalogenations of phenols and anilines in water employing new Lewis base adducts (LBAs) [DBUBr]⁺Br⁻ and [DBUI]⁺I⁻ as green reagents: a simple approach

Vijayalaxmi Gavinolla,

Swathi Thangalipalli,

Siddarama Goud Bandalla

et al.

Abstract: An operationally simple temperature dependant regioselective halogenation of phenols and anilines in water using readily accessible and highly stable Lewis Base Adducts (LBAs) is reported. These newly discovered LBAs [DBUBr]+Br-...

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2024

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Cited by 2 publications

References 97 publications

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Highly Practical Aqueous Phase Acylation of Phenols, Amines and Alcohols Employing New Green Acylation Reagents Derived From DBU

Thangalipalli,

Goud Bandalla,

Gavinolla

et al. 2024

ChemistrySelect

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Two new Lewis base adducts (LBAs) of DBU were prepared, isolated in grams scale and are employed as Green reagents for base free benzoylation and pivaloylation in water. The structures of these reagents are unambiguously confirmed and the practicality of these LBAs (transient species) in organic synthesis as operationally simple protecting reagents of various phenols, amines, and alcohols in water at ambient temperature is explored. The products are furnished in very good yields (up to 95 %) and are purified just by filtration followed by recrystallization thus avoiding column chromatography. The Lewis base, DBU is recycled and reused for the preparation of LBAs. The methodology is an environmentally benign due to aqueous phase, base free reaction, chromatography free purificatios, ambient temperature reactions and recycling DBU.

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Highly Practical Aqueous Phase Acylation of Phenols, Amines and Alcohols Employing New Green Acylation Reagents Derived From DBU

Thangalipalli,

Goud Bandalla,

Gavinolla

et al. 2024

ChemistrySelect

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8-Iodo-4-methyl-2-oxo-2H-chromen-7-yl Benzenesulfonate

Pulido-Moreno,

Parra-Tibocha,

Ladino-Bejarano

et al. 2024

Molbank

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We report a straightforward and efficient synthesis of 4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3a) and 8-iodo-4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3b) in good yields through an O-sulfonylation reaction of 7-hydroxy-2H-chromen-2-ones 1a and 1b with benzenesulfonyl chloride 2 mediated by triethylamine in dichloromethane at ambient temperature. The aryl sulfonyl esters were characterized using spectroscopic, spectrometric, and thermal analyses.

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A thermo-regulated highly regioselective mono and dihalogenations of phenols and anilines in water employing new Lewis base adducts (LBAs) [DBUBr]⁺Br⁻ and [DBUI]⁺I⁻ as green reagents: a simple approach

Abstract: An operationally simple temperature dependant regioselective halogenation of phenols and anilines in water using readily accessible and highly stable Lewis Base Adducts (LBAs) is reported. These newly discovered LBAs [DBUBr]+Br-...

Cited by 2 publications

References 97 publications

Highly Practical Aqueous Phase Acylation of Phenols, Amines and Alcohols Employing New Green Acylation Reagents Derived From DBU

Highly Practical Aqueous Phase Acylation of Phenols, Amines and Alcohols Employing New Green Acylation Reagents Derived From DBU

8-Iodo-4-methyl-2-oxo-2H-chromen-7-yl Benzenesulfonate

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