Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes
Utilization of waste-derived materials for industrially pertinent chemical transformations is highly challenging and offers sustainable solution to waste management. Despite several difficulties in the manufacture of aryl iodides (AIs), which are the fundamental substrates in organic synthesis, we r...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2021-10-01
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| Series: | Green Chemistry Letters and Reviews |
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| Online Access: | http://dx.doi.org/10.1080/17518253.2021.2006319 |
| _version_ | 1798019739045330944 |
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| author | Rama Moorthy Appa Bandameeda Ramesh Naidu Derangula Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana Jangam Lakshmidevi Katta Venkateswarlu |
| author_facet | Rama Moorthy Appa Bandameeda Ramesh Naidu Derangula Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana Jangam Lakshmidevi Katta Venkateswarlu |
| author_sort | Rama Moorthy Appa |
| collection | DOAJ |
| description | Utilization of waste-derived materials for industrially pertinent chemical transformations is highly challenging and offers sustainable solution to waste management. Despite several difficulties in the manufacture of aryl iodides (AIs), which are the fundamental substrates in organic synthesis, we report here, an added oxidant/metal/catalyst/additive and problematic solvent-free versatile and straightforward protocol for the synthesis of AIs using molecular iodine (I2) in water extract of pomegranate ash (WEPA). These transformations were performed at room temperature (rt) and the reactions takes place in 5–20 min to give 83–99% yields of AIs. WEPA was characterized by using XPS, EDX, XRF, XRD, and FTIR analysis and a plausible mechanism has been established based on these analyses along with some control experiments. Further, the products were purified by recrystallization technique. This work with intrinsic sustainability, high substrate feasibility, utilization of biorenewable catalystytic media, ease of execution and separation of products, and added oxidant/catalyst/metal and additive-free conditions may become one among the forefront sustainable procedures in making AIs. The use of waste-derived WEPA as catalystytic media for this iodination is the novelty of this method and may be used these AIs for further in-process transformations (e.g. cross-couplings, nucleophilic reactions, etc.) to access fine chemicals. |
| first_indexed | 2024-04-11T16:44:36Z |
| format | Article |
| id | doaj.art-10d2aafa346b42498495b5b82fc0eca7 |
| institution | Directory Open Access Journal |
| issn | 1751-8253 1751-7192 |
| language | English |
| last_indexed | 2024-04-11T16:44:36Z |
| publishDate | 2021-10-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Green Chemistry Letters and Reviews |
| spelling | doaj.art-10d2aafa346b42498495b5b82fc0eca72022-12-22T04:13:35ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922021-10-0114470071210.1080/17518253.2021.20063192006319Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenesRama Moorthy Appa0Bandameeda Ramesh Naidu1Derangula Venkateswarlu2Marlia M. Hanafiah3Sivarama Krishna Lakkaboyana4Jangam Lakshmidevi5Katta Venkateswarlu6Laboratory for Synthetic & Natural Products ChemistryLaboratory for Synthetic & Natural Products ChemistryCSIR-Indian Institute of Chemical TechnologyUniversiti Kebangsaan MalaysiaChulalongkorn UniversityLaboratory for Synthetic & Natural Products ChemistryLaboratory for Synthetic & Natural Products ChemistryUtilization of waste-derived materials for industrially pertinent chemical transformations is highly challenging and offers sustainable solution to waste management. Despite several difficulties in the manufacture of aryl iodides (AIs), which are the fundamental substrates in organic synthesis, we report here, an added oxidant/metal/catalyst/additive and problematic solvent-free versatile and straightforward protocol for the synthesis of AIs using molecular iodine (I2) in water extract of pomegranate ash (WEPA). These transformations were performed at room temperature (rt) and the reactions takes place in 5–20 min to give 83–99% yields of AIs. WEPA was characterized by using XPS, EDX, XRF, XRD, and FTIR analysis and a plausible mechanism has been established based on these analyses along with some control experiments. Further, the products were purified by recrystallization technique. This work with intrinsic sustainability, high substrate feasibility, utilization of biorenewable catalystytic media, ease of execution and separation of products, and added oxidant/catalyst/metal and additive-free conditions may become one among the forefront sustainable procedures in making AIs. The use of waste-derived WEPA as catalystytic media for this iodination is the novelty of this method and may be used these AIs for further in-process transformations (e.g. cross-couplings, nucleophilic reactions, etc.) to access fine chemicals.http://dx.doi.org/10.1080/17518253.2021.2006319i2-wepautilization of waste(hetero)aryl iodidessustainable iodinationnon-chromatographic purification |
| spellingShingle | Rama Moorthy Appa Bandameeda Ramesh Naidu Derangula Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana Jangam Lakshmidevi Katta Venkateswarlu Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes Green Chemistry Letters and Reviews i2-wepa utilization of waste (hetero)aryl iodides sustainable iodination non-chromatographic purification |
| title | Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes |
| title_full | Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes |
| title_fullStr | Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes |
| title_full_unstemmed | Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes |
| title_short | Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes |
| title_sort | water extract of pomegranate ash i2 as sustainable system for external oxidant metal catalyst free oxidative iodination of hetero arenes |
| topic | i2-wepa utilization of waste (hetero)aryl iodides sustainable iodination non-chromatographic purification |
| url | http://dx.doi.org/10.1080/17518253.2021.2006319 |
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