A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract
The application of waste biomass-derived materials to synthetic chemistry is a remarkable achievement, and the use of aqueous media is further advancement. The switch towards earth's abundant metals like cobalt/copper/iron/nickel from precious palladium in C–C coupling reactions is also a high...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2022-07-01
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| Series: | Green Chemistry Letters and Reviews |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/17518253.2022.2109433 |
| _version_ | 1798015852656721920 |
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| author | Jangam Lakshmidevi Bandameeda Ramesh Naidu Katta Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana |
| author_facet | Jangam Lakshmidevi Bandameeda Ramesh Naidu Katta Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana |
| author_sort | Jangam Lakshmidevi |
| collection | DOAJ |
| description | The application of waste biomass-derived materials to synthetic chemistry is a remarkable achievement, and the use of aqueous media is further advancement. The switch towards earth's abundant metals like cobalt/copper/iron/nickel from precious palladium in C–C coupling reactions is also a high throughput in the global sustainability perspective. Herein, we describe a CuCl-catalyzed homocoupling of (hetero)arylboronic acids (HABAs) in water extract of pomegranate ash (WEPA) with low E-factor of 1.25 without including the column chromatographic separation of products, which helped in understanding the effectiveness of this method on comparison to reported protocols lacking amounts of silica gel and eluents, however, it was 171.64 by including column purification. The reactions are conducted at room temperature to deliver self-coupling products with 90–99% yields in 10–45 min under precious metal, ligand, non-renewable base, toxic/problematic organic solvent and added oxidant-free conditions. A wide range of substrates were screened with aryl and heteroaryl moieties containing diversified functional groups. The substitution of earth's rare metals-based catalysts by abundant copper, exploration of waste to state-of-the-art C–C coupling, use of biorenewable base, aqueous media, ambient conditions, operational simplicity, excellent yields of biaryls and quick reactions are the noteworthy advantages of this protocol. |
| first_indexed | 2024-04-11T15:41:23Z |
| format | Article |
| id | doaj.art-69a79b9c83a141138ddc411d46e2feac |
| institution | Directory Open Access Journal |
| issn | 1751-8253 1751-7192 |
| language | English |
| last_indexed | 2024-04-11T15:41:23Z |
| publishDate | 2022-07-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Green Chemistry Letters and Reviews |
| spelling | doaj.art-69a79b9c83a141138ddc411d46e2feac2022-12-22T04:15:47ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922022-07-0115352953610.1080/17518253.2022.2109433A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extractJangam Lakshmidevi0Bandameeda Ramesh Naidu1Katta Venkateswarlu2Marlia M. Hanafiah3Sivarama Krishna Lakkaboyana4Laboratory for Synthetic & Natural Products Chemistry, Department of Chemistry, Yogi Vemana University, Kadapa, IndiaLaboratory for Synthetic & Natural Products Chemistry, Department of Chemistry, Yogi Vemana University, Kadapa, IndiaLaboratory for Synthetic & Natural Products Chemistry, Department of Chemistry, Yogi Vemana University, Kadapa, IndiaDepartment of Earth Sciences and Environment, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, MalaysiaDepartment of Chemistry, Vel Tech Rangarajan Dr. Sagunthala R & D Institute of Science and Technology, Chennai, IndiaThe application of waste biomass-derived materials to synthetic chemistry is a remarkable achievement, and the use of aqueous media is further advancement. The switch towards earth's abundant metals like cobalt/copper/iron/nickel from precious palladium in C–C coupling reactions is also a high throughput in the global sustainability perspective. Herein, we describe a CuCl-catalyzed homocoupling of (hetero)arylboronic acids (HABAs) in water extract of pomegranate ash (WEPA) with low E-factor of 1.25 without including the column chromatographic separation of products, which helped in understanding the effectiveness of this method on comparison to reported protocols lacking amounts of silica gel and eluents, however, it was 171.64 by including column purification. The reactions are conducted at room temperature to deliver self-coupling products with 90–99% yields in 10–45 min under precious metal, ligand, non-renewable base, toxic/problematic organic solvent and added oxidant-free conditions. A wide range of substrates were screened with aryl and heteroaryl moieties containing diversified functional groups. The substitution of earth's rare metals-based catalysts by abundant copper, exploration of waste to state-of-the-art C–C coupling, use of biorenewable base, aqueous media, ambient conditions, operational simplicity, excellent yields of biaryls and quick reactions are the noteworthy advantages of this protocol.https://www.tandfonline.com/doi/10.1080/17518253.2022.2109433CuCl-WEPAwaste volarization(hetero)arylboronic acidsoxidative self-couplingsymmetrical biarylslow E-factor |
| spellingShingle | Jangam Lakshmidevi Bandameeda Ramesh Naidu Katta Venkateswarlu Marlia M. Hanafiah Sivarama Krishna Lakkaboyana A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract Green Chemistry Letters and Reviews CuCl-WEPA waste volarization (hetero)arylboronic acids oxidative self-coupling symmetrical biaryls low E-factor |
| title | A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract |
| title_full | A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract |
| title_fullStr | A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract |
| title_full_unstemmed | A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract |
| title_short | A quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract |
| title_sort | quick and low e factor waste valorization procedure for cucl catalyzed oxidative self coupling of hetero arylboronic acid in pomegranate peel ash extract |
| topic | CuCl-WEPA waste volarization (hetero)arylboronic acids oxidative self-coupling symmetrical biaryls low E-factor |
| url | https://www.tandfonline.com/doi/10.1080/17518253.2022.2109433 |
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