Ferrocenium complex aided <i>O</i>-glycosylation of glycosyl halides

Talasila, Deva Saroja; Bauer, Eike B.

doi:10.1039/d1ra05788j

Cited by 2 publications

(2 citation statements)

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“…[7] These brominated donors find the synthetic utility in the construction of glycosidic linkage with different acceptors. [8,9] Halogenation of heterocyclic compounds is another attractive approach for activating a particular position, [10] and carrying out different coupling reactions like Suzuki-Miyaura, [11] Sonogashira reactions, [12] and Heck coupling [13] to generate medicinally important derivatives. To synthesize brominated glycals and heterocyclic scaffolds, various strategies were developed [14][15][16][17][18][19] in the past such as C. Chiappe and co-workers studied dihalogenation in alkene by using elemental bromine and ionic solvents.…”

Section: Introductionmentioning

confidence: 99%

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TBA−Br and Selectfluor Mediated Bromination of Glycals and Heterocyclic Compounds: Substrate Scope and Synthetic Utility

Maheshwari,

Hussain

2023

ChemistrySelect

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Herein, we have devised a metal‐free stereoselective protocol mediated by selectfluor for the dibromination of sugar enol‐ethers and monobromination of heterocyclic compounds. The dibromination of glycals was achieved within 5 minutes at room temperature with excellent yields. The tolerance of various protecting groups such as acetyl, benzyl, and silyl in sugars was checked. When the same reagent system was applied to substituted indoles and chromones 3‐brominated products were obtained but at elevated temperatures. The synthetic utility of the methodology was demonstrated by using the brominated indoles and chromones to synthesize the 3‐aryl indoles and isoflavones respectively via Suzuki‐Miyura cross‐coupling reactions.

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Section: Introductionmentioning

confidence: 99%

“…Halogenated sugars were also utilized for the synthesis of deoxy sugars, which shows wide medicinal applications [7] . These brominated donors find the synthetic utility in the construction of glycosidic linkage with different acceptors [8,9] …”

Section: Introductionmentioning

confidence: 99%