Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source
Carbon dioxide (CO2) is one of the most important materials as renewable chemical feedstock. In this review, the Co- and Rh-catalyzed transformation of CO2 via carbon–carbon bond-forming reactions is summarized. Combinations of metals (cobalt or rhodium), substrates, and reducing agents realize effi...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.221 |
| _version_ | 1818344001175027712 |
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| author | Tetsuaki Fujihara Yasushi Tsuji |
| author_facet | Tetsuaki Fujihara Yasushi Tsuji |
| author_sort | Tetsuaki Fujihara |
| collection | DOAJ |
| description | Carbon dioxide (CO2) is one of the most important materials as renewable chemical feedstock. In this review, the Co- and Rh-catalyzed transformation of CO2 via carbon–carbon bond-forming reactions is summarized. Combinations of metals (cobalt or rhodium), substrates, and reducing agents realize efficient carboxylation reactions using CO2. The carboxylation of propargyl acetates and alkenyl triflates using cobalt complexes as well as the cobalt-catalyzed reductive carboxylation of α,β-unsaturated nitriles and carboxyamides in the presence of Et2Zn proceed. A Co complex has been demonstrated to act as an efficient catalyst in the carboxylation of allylic C(sp3)–H bonds. Employing zinc as the reductant, carboxyzincation and the four-component coupling reaction between alkyne, acrylates, CO2, and zinc occur efficiently. Rh complexes also catalyze the carboxylation of arylboronic esters, C(sp2)–H carboxylation of aromatic compounds, and hydrocarboxylation of styrene derivatives. The Rh-catalyzed [2 + 2 + 2] cycloaddition of diynes and CO2 proceeds to afford pyrones. |
| first_indexed | 2024-12-13T16:39:32Z |
| format | Article |
| id | doaj.art-67db093557be4eb9898a555785cd52ff |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T16:39:32Z |
| publishDate | 2018-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-67db093557be4eb9898a555785cd52ff2022-12-21T23:38:18ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-09-011412435246010.3762/bjoc.14.2211860-5397-14-221Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 sourceTetsuaki Fujihara0Yasushi Tsuji1Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, JapanDepartment of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, JapanCarbon dioxide (CO2) is one of the most important materials as renewable chemical feedstock. In this review, the Co- and Rh-catalyzed transformation of CO2 via carbon–carbon bond-forming reactions is summarized. Combinations of metals (cobalt or rhodium), substrates, and reducing agents realize efficient carboxylation reactions using CO2. The carboxylation of propargyl acetates and alkenyl triflates using cobalt complexes as well as the cobalt-catalyzed reductive carboxylation of α,β-unsaturated nitriles and carboxyamides in the presence of Et2Zn proceed. A Co complex has been demonstrated to act as an efficient catalyst in the carboxylation of allylic C(sp3)–H bonds. Employing zinc as the reductant, carboxyzincation and the four-component coupling reaction between alkyne, acrylates, CO2, and zinc occur efficiently. Rh complexes also catalyze the carboxylation of arylboronic esters, C(sp2)–H carboxylation of aromatic compounds, and hydrocarboxylation of styrene derivatives. The Rh-catalyzed [2 + 2 + 2] cycloaddition of diynes and CO2 proceeds to afford pyrones.https://doi.org/10.3762/bjoc.14.221carbon dioxidecarboxylationcobalthomogeneous catalystsrhodium |
| spellingShingle | Tetsuaki Fujihara Yasushi Tsuji Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source Beilstein Journal of Organic Chemistry carbon dioxide carboxylation cobalt homogeneous catalysts rhodium |
| title | Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source |
| title_full | Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source |
| title_fullStr | Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source |
| title_full_unstemmed | Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source |
| title_short | Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source |
| title_sort | cobalt and rhodium catalyzed carboxylation using carbon dioxide as the c1 source |
| topic | carbon dioxide carboxylation cobalt homogeneous catalysts rhodium |
| url | https://doi.org/10.3762/bjoc.14.221 |
| work_keys_str_mv | AT tetsuakifujihara cobaltandrhodiumcatalyzedcarboxylationusingcarbondioxideasthec1source AT yasushitsuji cobaltandrhodiumcatalyzedcarboxylationusingcarbondioxideasthec1source |