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Oxidative Iododeborylation Reaction of (Hetero)arylboronic Acids in Water Extract of Pomegranate Ash: A Novel and Sustainable Synthesis of Iodo(hetero)arenes

Oxidative Iododeborylation Reaction of (Hetero)arylboronic Acids in Water Extract of Pomegranate... The exploitation of organic waste-derived products in industrially relevant chemical transformations is a brainstorming and indispensible task in chemical synthesis. Indeed, the ipso-functionalization of (hetero)arylboronic acids [(H)ABAs] under (transition)metal free condisitions is a challenging and intended goal in synthetic chemistry. Further, the synthesis of (hetero)aryl iodides [(H)AIs] under mild and benign conditions is urgently needed task since these are the highly reactive substrates in several state-of-the-art cross-coupling and aromatic functionalization reactions and a very few methods/reagents are available for their synthesis. In this article we have disclosed a mild and effective process for the (H)AIs synthesis via ipso-functionalization of (H)ABAs using water extract of pomegranate peel ash (WEPA) and environmentally benign iodinating agent such as molecular iodine (I2) under external oxidant/(transition)metal/base/additive/organic solvent free conditions. The (H)AIs are formed with high regioselctivity using this protocol has operational simplicity display exceptional functional group compatibility. Present (H)AIs synthesis avoid additional substances (including metals) as oxidizing reagents, additives/surfactants and catalysts, thus making this procedure as a highly sustainable asset using biorenewable waste based aqueous extract as catalytic media.Graphical Abstract[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Waste and Biomass Valorization Springer Journals

Oxidative Iododeborylation Reaction of (Hetero)arylboronic Acids in Water Extract of Pomegranate Ash: A Novel and Sustainable Synthesis of Iodo(hetero)arenes

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References (76)

Publisher
Springer Journals
Copyright
Copyright © The Author(s), under exclusive licence to Springer Nature B.V. 2021
ISSN
1877-2641
eISSN
1877-265X
DOI
10.1007/s12649-021-01647-z
Publisher site
See Article on Publisher Site

Abstract

The exploitation of organic waste-derived products in industrially relevant chemical transformations is a brainstorming and indispensible task in chemical synthesis. Indeed, the ipso-functionalization of (hetero)arylboronic acids [(H)ABAs] under (transition)metal free condisitions is a challenging and intended goal in synthetic chemistry. Further, the synthesis of (hetero)aryl iodides [(H)AIs] under mild and benign conditions is urgently needed task since these are the highly reactive substrates in several state-of-the-art cross-coupling and aromatic functionalization reactions and a very few methods/reagents are available for their synthesis. In this article we have disclosed a mild and effective process for the (H)AIs synthesis via ipso-functionalization of (H)ABAs using water extract of pomegranate peel ash (WEPA) and environmentally benign iodinating agent such as molecular iodine (I2) under external oxidant/(transition)metal/base/additive/organic solvent free conditions. The (H)AIs are formed with high regioselctivity using this protocol has operational simplicity display exceptional functional group compatibility. Present (H)AIs synthesis avoid additional substances (including metals) as oxidizing reagents, additives/surfactants and catalysts, thus making this procedure as a highly sustainable asset using biorenewable waste based aqueous extract as catalytic media.Graphical Abstract[graphic not available: see fulltext]

Journal

Waste and Biomass ValorizationSpringer Journals

Published: Apr 1, 2022

Keywords: Waste valorization; (Hetero)aryl iodides; Molecular iodine; WEPA; Biorenewable resource

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