NaIO<sub>4</sub>/KI/NaCl: A New Reagent System for Iodination of Activated Aromatics Through in situ Generation of Iodine Monochloride.

Emmanuvel, Lourdusamy; Shukla, Ravi; Sudalai, Arumugam; Suryavanshi, Gurunath; Sivaram, Swaminathan

doi:10.1002/chin.200643069

Cited by 2 publications

(2 citation statements)

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“…Iodination of 4‐hydroxybenzaldehyde followed the method previously reported (Emmanuvel et al ., ) with slight modification. To a mixture of 4‐hydroxybenzaldehyde (5.00 g, 41 mmol), NaIO 4 (8.76 g, 41 mmol) and NaCl (2.39 g, 41 mmol) in 150 ml of acetic acid:H 2 O (9:1, v/v) was slowly added KI (6.80 g, 41 mmol).…”

Section: Methodsmentioning

confidence: 99%

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

et al. 2016

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SUMMARYTricin [5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one], a flavone, was recently established as an authentic monomer in grass lignification that likely functions as a nucleation site. It is linked onto lignin as an aryl alkyl ether by radical coupling with monolignols or their acylated analogs. However, the level of tricin that incorporates into lignin remains unclear. Herein, three lignin characterization methods: acidolysis; thioacidolysis; and derivatization followed by reductive cleavage; were applied to quantitatively assess the amount of lignin-integrated tricin. Their efficiencies at cleaving the tricin-(4 0 -O-b)-ether bonds and the degradation of tricin under the corresponding reaction conditions were evaluated. A hexadeuterated tricin analog was synthesized as an internal standard for accurate quantitation purposes. Thioacidolysis proved to be the most efficient method, liberating more than 91% of the tricin with little degradation. A survey of different seed-plant species for the occurrence and content of tricin showed that it is widely distributed in the lignin from species in the family Poaceae (order Poales). Tricin occurs at low levels in some commelinid monocotyledon families outside the Poaceae, such as the Arecaceae (the palms, order Arecales) and Bromeliaceae (Poales), and the non-commelinid monocotyledon family Orchidaceae (Orchidales). One eudicotyledon was found to have tricin (Medicago sativa, Fabaceae). The content of lignin-integrated tricin is much higher than the extractable tricin level in all cases. Lignins, including waste lignin streams from biomass processing, could therefore provide a large and alternative source of this valuable flavone, reducing the costs, and encouraging studies into its application beyond its current roles.

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Section: Methodsmentioning

confidence: 99%

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

et al. 2016

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“…Moreover, the aryl iodide product can potentially be further oxidized into hyperiodide species (Banik et al, 2016), leading to undesired by-products. To our delight, such overoxidation was not observed in this reaction (Emmanuvel et al, 2006). Selected substrates were investigated, and all afforded the products in moderate to excellent yield, including aniline (2-43, 2-45), phenol (2-44), and heteroarene (2-46, 2-47).…”

Section: Substrate Scope Of Tungstate-catalyzed Oxidative Chlorination and Iodinationmentioning

confidence: 88%

Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition

Liao

et al. 2020

iScience

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Aryl halide (Br, Cl, I) is among the most important compounds in pharmaceutical industry, material science, and agrochemistry, broadly utilized in diverse transformations. Tremendous approaches have been established to prepare this scaffold; however, many of them suffer from atom economy, harsh condition, inability to be scaled up, or cost-unfriendly reagents and catalysts. Inspired by vanadium haloperoxidases herein we presented a biomimetic approach for halogenation (Br, Cl, I) of (hetero)arene catalyzed by tungstate under mild pH in a costefficient and environment-and operation-friendly manner. Broad substrates, diverse functional group tolerance, and good chemo-and regioselectivities were observed, even in late-stage halogenation of complex molecules. Moreover, this approach can be scaled up to over 100 g without time-consuming and costly column purification. Several drugs and key precursors for drugs bearing aryl halides (Br, Cl, I) have been conveniently prepared based on our approach.

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NaIO₄/KI/NaCl: A New Reagent System for Iodination of Activated Aromatics Through in situ Generation of Iodine Monochloride.

Cited by 2 publications

References 1 publication

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition

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NaIO4/KI/NaCl: A New Reagent System for Iodination of Activated Aromatics Through in situ Generation of Iodine Monochloride.

Cited by 2 publications

References 1 publication

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition

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NaIO₄/KI/NaCl: A New Reagent System for Iodination of Activated Aromatics Through in situ Generation of Iodine Monochloride.