Photoinduced oxidative cyclization of dithienylarenes
A photoinduced electrocyclization followed by aerobic oxidation of 1,2-dithienylarene derivatives is described as a greener alternative to direct aryl-aryl couplings. The formation of the naphthodithiophene type products was monitored by UV–vis spectroscopy. Naphthodithiophenes with different struct...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-06-01
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| Series: | Tetrahedron Green Chem |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2773223125000159 |
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| author | Barnabás Zsignár-Nagy Viktória Kümmel Tamás Gazdag Péter J. Mayer Zsófia Bokor Tamás Holczbauer Gábor London |
| author_facet | Barnabás Zsignár-Nagy Viktória Kümmel Tamás Gazdag Péter J. Mayer Zsófia Bokor Tamás Holczbauer Gábor London |
| author_sort | Barnabás Zsignár-Nagy |
| collection | DOAJ |
| description | A photoinduced electrocyclization followed by aerobic oxidation of 1,2-dithienylarene derivatives is described as a greener alternative to direct aryl-aryl couplings. The formation of the naphthodithiophene type products was monitored by UV–vis spectroscopy. Naphthodithiophenes with different structural features and electronic characters were accessed. Oxidative cyclization using the combination of BF3·Et2O and DDQ was a complementary approach to confirm the formation of the desired products. The method was also applicable to 2,3-dithienylbiphenylene having a backbone with antiaromatic character. |
| format | Article |
| id | doaj-art-ab1ee2c9e2754ff1891c81f7cff02d30 |
| institution | Kabale University |
| issn | 2773-2231 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Green Chem |
| spelling | doaj-art-ab1ee2c9e2754ff1891c81f7cff02d302025-08-20T03:45:10ZengElsevierTetrahedron Green Chem2773-22312025-06-01510007610.1016/j.tgchem.2025.100076Photoinduced oxidative cyclization of dithienylarenesBarnabás Zsignár-Nagy0Viktória Kümmel1Tamás Gazdag2Péter J. Mayer3Zsófia Bokor4Tamás Holczbauer5Gábor London6Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, Hungary; Hevesy György PhD School of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, 1117, Budapest, HungaryInstitute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, HungaryInstitute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, HungaryInstitute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, HungaryInstitute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, HungaryInstitute of Organic Chemistry, Centre for Structural Science, HUN-REN Research Centre for Natural Sciences, Magyar Tudósok krt. 2, 1117, Budapest, HungaryInstitute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok krt. 2., 1117, Budapest, Hungary; Corresponding author.''A photoinduced electrocyclization followed by aerobic oxidation of 1,2-dithienylarene derivatives is described as a greener alternative to direct aryl-aryl couplings. The formation of the naphthodithiophene type products was monitored by UV–vis spectroscopy. Naphthodithiophenes with different structural features and electronic characters were accessed. Oxidative cyclization using the combination of BF3·Et2O and DDQ was a complementary approach to confirm the formation of the desired products. The method was also applicable to 2,3-dithienylbiphenylene having a backbone with antiaromatic character.http://www.sciencedirect.com/science/article/pii/S2773223125000159ThiophenePhotochemistryMallory reactionHeterocycleGreen chemistry |
| spellingShingle | Barnabás Zsignár-Nagy Viktória Kümmel Tamás Gazdag Péter J. Mayer Zsófia Bokor Tamás Holczbauer Gábor London Photoinduced oxidative cyclization of dithienylarenes Tetrahedron Green Chem Thiophene Photochemistry Mallory reaction Heterocycle Green chemistry |
| title | Photoinduced oxidative cyclization of dithienylarenes |
| title_full | Photoinduced oxidative cyclization of dithienylarenes |
| title_fullStr | Photoinduced oxidative cyclization of dithienylarenes |
| title_full_unstemmed | Photoinduced oxidative cyclization of dithienylarenes |
| title_short | Photoinduced oxidative cyclization of dithienylarenes |
| title_sort | photoinduced oxidative cyclization of dithienylarenes |
| topic | Thiophene Photochemistry Mallory reaction Heterocycle Green chemistry |
| url | http://www.sciencedirect.com/science/article/pii/S2773223125000159 |
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