Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions
Acetic acid as catalyst in pure water was found to be an excellent reaction medium for the direct dehydrative functionalization of π-activated alcohols using a wide variety of interesting C-, P-, and S-centered nucleophiles, such as indoles, pyrrole, anilines, 1,3-dicarbonyl compounds, diphenyl phos...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-01-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535218300315 |
| _version_ | 1818021738286415872 |
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| author | Rosa Ortiz Alessandro Koukouras Eugenia Marqués-López Raquel P. Herrera |
| author_facet | Rosa Ortiz Alessandro Koukouras Eugenia Marqués-López Raquel P. Herrera |
| author_sort | Rosa Ortiz |
| collection | DOAJ |
| description | Acetic acid as catalyst in pure water was found to be an excellent reaction medium for the direct dehydrative functionalization of π-activated alcohols using a wide variety of interesting C-, P-, and S-centered nucleophiles, such as indoles, pyrrole, anilines, 1,3-dicarbonyl compounds, diphenyl phosphite and pyridine-2-thiol. The smooth reaction conditions, along with high yields, short reaction times, clean reaction crudes, an easy product isolation procedure, plus the reusability of the catalyst and the use of no excess of nucleophiles, make this approach an atom economical, green and appealing method to efficiently trap carbocations in pure water, leading to new Csp3X bonds (X = Csp2, Csp3, P and S). Keywords: π-Activated alcohols, Brønsted acid, Carbocation, Dehydrative substitution, Water |
| first_indexed | 2024-04-14T08:23:01Z |
| format | Article |
| id | doaj.art-40b9ca394bd94b9b93c9cb7e3f671052 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-14T08:23:01Z |
| publishDate | 2020-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-40b9ca394bd94b9b93c9cb7e3f6710522022-12-22T02:04:10ZengElsevierArabian Journal of Chemistry1878-53522020-01-0113118661873Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditionsRosa Ortiz0Alessandro Koukouras1Eugenia Marqués-López2Raquel P. Herrera3Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/ Pedro Cerbuna 12, 50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/ Pedro Cerbuna 12, 50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/ Pedro Cerbuna 12, 50009 Zaragoza, SpainCorresponding author.; Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/ Pedro Cerbuna 12, 50009 Zaragoza, SpainAcetic acid as catalyst in pure water was found to be an excellent reaction medium for the direct dehydrative functionalization of π-activated alcohols using a wide variety of interesting C-, P-, and S-centered nucleophiles, such as indoles, pyrrole, anilines, 1,3-dicarbonyl compounds, diphenyl phosphite and pyridine-2-thiol. The smooth reaction conditions, along with high yields, short reaction times, clean reaction crudes, an easy product isolation procedure, plus the reusability of the catalyst and the use of no excess of nucleophiles, make this approach an atom economical, green and appealing method to efficiently trap carbocations in pure water, leading to new Csp3X bonds (X = Csp2, Csp3, P and S). Keywords: π-Activated alcohols, Brønsted acid, Carbocation, Dehydrative substitution, Waterhttp://www.sciencedirect.com/science/article/pii/S1878535218300315 |
| spellingShingle | Rosa Ortiz Alessandro Koukouras Eugenia Marqués-López Raquel P. Herrera Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions Arabian Journal of Chemistry |
| title | Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions |
| title_full | Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions |
| title_fullStr | Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions |
| title_full_unstemmed | Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions |
| title_short | Functionalization of π-activated alcohols by trapping carbocations in pure water under smooth conditions |
| title_sort | functionalization of π activated alcohols by trapping carbocations in pure water under smooth conditions |
| url | http://www.sciencedirect.com/science/article/pii/S1878535218300315 |
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