A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide
The catalytic system of triphenylphosphine oxide and phthaloyl dichloride catalysing conversion of aldehydes to 1,1-dichlorides is reported. The reaction proceeds via a P (V) catalysis manifold in which triphenylphosphine oxide turnover is achieved using phthaloyl dichloride as a consumable reagent....
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| Format: | Article |
| Language: | English |
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Uralʹskij federalʹnyj universitet imeni pervogo Prezidenta Rossii B.N. Elʹcina
2022-03-01
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| Series: | Chimica Techno Acta |
| Subjects: | |
| Online Access: | https://journals.urfu.ru/index.php/chimtech/article/view/5713 |
| _version_ | 1818536141006045184 |
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| author | D. A. Shipilovskikh M. F. Konkova I. P. Nikonov M. M. Gladysheva S. A. Shipilovskikh |
| author_facet | D. A. Shipilovskikh M. F. Konkova I. P. Nikonov M. M. Gladysheva S. A. Shipilovskikh |
| author_sort | D. A. Shipilovskikh |
| collection | DOAJ |
| description | The catalytic system of triphenylphosphine oxide and phthaloyl dichloride catalysing conversion of aldehydes to 1,1-dichlorides is reported. The reaction proceeds via a P (V) catalysis manifold in which triphenylphosphine oxide turnover is achieved using phthaloyl dichloride as a consumable reagent. The application of the developed method on substrates of different structures was demonstrated. We showed the use of unsaturated compounds, including aromatics with and without electron donating / withdrawing groups, as well as saturated aliphatic compounds. The possibility of using the developed method on a gram scale was also demonstrated with the deoxydichlorination reaction of 0.03 mol of benzaldehyde catalyzed by triphenylphosphine oxide as an example. The proposed method may be of interest for the production of different herbicides, insecticides and fungicides for the agricultural industry. |
| first_indexed | 2024-12-11T18:34:07Z |
| format | Article |
| id | doaj.art-1510eff16753446eb72986d48533c1f0 |
| institution | Directory Open Access Journal |
| issn | 2411-1414 |
| language | English |
| last_indexed | 2024-12-11T18:34:07Z |
| publishDate | 2022-03-01 |
| publisher | Uralʹskij federalʹnyj universitet imeni pervogo Prezidenta Rossii B.N. Elʹcina |
| record_format | Article |
| series | Chimica Techno Acta |
| spelling | doaj.art-1510eff16753446eb72986d48533c1f02022-12-22T00:54:49ZengUralʹskij federalʹnyj universitet imeni pervogo Prezidenta Rossii B.N. ElʹcinaChimica Techno Acta2411-14142022-03-019210.15826/chimtech.2022.9.2.024348A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxideD. A. Shipilovskikh0M. F. Konkova1I. P. Nikonov2M. M. Gladysheva3S. A. Shipilovskikh4Perm State University; Perm National Research Polytechnic UniversityPerm State UniversityPerm State UniversityPerm State UniversityPerm State University; ITMO UniversityThe catalytic system of triphenylphosphine oxide and phthaloyl dichloride catalysing conversion of aldehydes to 1,1-dichlorides is reported. The reaction proceeds via a P (V) catalysis manifold in which triphenylphosphine oxide turnover is achieved using phthaloyl dichloride as a consumable reagent. The application of the developed method on substrates of different structures was demonstrated. We showed the use of unsaturated compounds, including aromatics with and without electron donating / withdrawing groups, as well as saturated aliphatic compounds. The possibility of using the developed method on a gram scale was also demonstrated with the deoxydichlorination reaction of 0.03 mol of benzaldehyde catalyzed by triphenylphosphine oxide as an example. The proposed method may be of interest for the production of different herbicides, insecticides and fungicides for the agricultural industry.https://journals.urfu.ru/index.php/chimtech/article/view/5713aldehydeslewis base catalysisorganocatalysistriphenylphosphine oxidenucleophilic substitutionagricultural chemistry |
| spellingShingle | D. A. Shipilovskikh M. F. Konkova I. P. Nikonov M. M. Gladysheva S. A. Shipilovskikh A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide Chimica Techno Acta aldehydes lewis base catalysis organocatalysis triphenylphosphine oxide nucleophilic substitution agricultural chemistry |
| title | A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide |
| title_full | A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide |
| title_fullStr | A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide |
| title_full_unstemmed | A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide |
| title_short | A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide |
| title_sort | method of mild deoxydichlorination of aldehydes catalyzed by triphenylphosphine oxide |
| topic | aldehydes lewis base catalysis organocatalysis triphenylphosphine oxide nucleophilic substitution agricultural chemistry |
| url | https://journals.urfu.ru/index.php/chimtech/article/view/5713 |
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