Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters
The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. The ability to address this limitation, using high energy sensitizers, would repres...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.69 |
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| author | Lewis McGhie Hannah M. Kortman Jenna Rumpf Peter H. Seeberger John J. Molloy |
| author_facet | Lewis McGhie Hannah M. Kortman Jenna Rumpf Peter H. Seeberger John J. Molloy |
| author_sort | Lewis McGhie |
| collection | DOAJ |
| description | The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. The ability to address this limitation, using high energy sensitizers, would represent an attractive platform for future reaction design. Here, we disclose the photoactivation of simple alkenylboronic esters established using alkene scrambling as a rapid reaction probe to identify a suitable catalyst and boron motif. Cyclic voltammetry, UV–vis analysis, and control reactions support sensitization, enabling an intramolecular [2 + 2] cycloaddition to be realized accessing 3D bicyclic fragments containing a boron handle. |
| format | Article |
| id | doaj-art-8cc49a8b93e1454c8eff315763cfcb7c |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-8cc49a8b93e1454c8eff315763cfcb7c2025-08-20T01:47:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-04-0121185486310.3762/bjoc.21.691860-5397-21-69Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic estersLewis McGhie0Hannah M. Kortman1Jenna Rumpf2Peter H. Seeberger3John J. Molloy4Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. The ability to address this limitation, using high energy sensitizers, would represent an attractive platform for future reaction design. Here, we disclose the photoactivation of simple alkenylboronic esters established using alkene scrambling as a rapid reaction probe to identify a suitable catalyst and boron motif. Cyclic voltammetry, UV–vis analysis, and control reactions support sensitization, enabling an intramolecular [2 + 2] cycloaddition to be realized accessing 3D bicyclic fragments containing a boron handle.https://doi.org/10.3762/bjoc.21.69boroncatalysis[2 + 2] cycloadditionenergy transferphotochemistry |
| spellingShingle | Lewis McGhie Hannah M. Kortman Jenna Rumpf Peter H. Seeberger John J. Molloy Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters Beilstein Journal of Organic Chemistry boron catalysis [2 + 2] cycloaddition energy transfer photochemistry |
| title | Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters |
| title_full | Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters |
| title_fullStr | Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters |
| title_full_unstemmed | Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters |
| title_short | Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters |
| title_sort | light enabled intramolecular 2 2 cycloaddition via photoactivation of simple alkenylboronic esters |
| topic | boron catalysis [2 + 2] cycloaddition energy transfer photochemistry |
| url | https://doi.org/10.3762/bjoc.21.69 |
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