Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system
Abstract Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp 3)-H bonds. While inert, the activation of C(sp 3)-H via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include the excessive use of...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-09-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-023-00947-w |
| _version_ | 1797577610159456256 |
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| author | Hyotaik Kang Lida Tan Jing-Tan Han Chia-Yu Huang Hui Su Aleksei Kavun Chao-Jun Li |
| author_facet | Hyotaik Kang Lida Tan Jing-Tan Han Chia-Yu Huang Hui Su Aleksei Kavun Chao-Jun Li |
| author_sort | Hyotaik Kang |
| collection | DOAJ |
| description | Abstract Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp 3)-H bonds. While inert, the activation of C(sp 3)-H via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include the excessive use of oxidants and alkanes that impede scope. We herein show the use of gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst to enable alkyl C(sp 3 )-H in conjunction with the catalytic use of simple photosensitizer, benzophenone, to promote the desired alkyl radical generation. The dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild and chemical oxidant-free conditions. |
| first_indexed | 2024-03-10T22:10:30Z |
| format | Article |
| id | doaj.art-90e12bb5aafd42cda3d6658a4b25c066 |
| institution | Directory Open Access Journal |
| issn | 2399-3669 |
| language | English |
| last_indexed | 2024-03-10T22:10:30Z |
| publishDate | 2023-09-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj.art-90e12bb5aafd42cda3d6658a4b25c0662023-11-19T12:37:28ZengNature PortfolioCommunications Chemistry2399-36692023-09-01611910.1038/s42004-023-00947-wAcceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer systemHyotaik Kang0Lida Tan1Jing-Tan Han2Chia-Yu Huang3Hui Su4Aleksei Kavun5Chao-Jun Li6Department of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityDepartment of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill UniversityAbstract Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp 3)-H bonds. While inert, the activation of C(sp 3)-H via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include the excessive use of oxidants and alkanes that impede scope. We herein show the use of gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst to enable alkyl C(sp 3 )-H in conjunction with the catalytic use of simple photosensitizer, benzophenone, to promote the desired alkyl radical generation. The dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild and chemical oxidant-free conditions.https://doi.org/10.1038/s42004-023-00947-w |
| spellingShingle | Hyotaik Kang Lida Tan Jing-Tan Han Chia-Yu Huang Hui Su Aleksei Kavun Chao-Jun Li Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system Communications Chemistry |
| title | Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system |
| title_full | Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system |
| title_fullStr | Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system |
| title_full_unstemmed | Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system |
| title_short | Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system |
| title_sort | acceptorless cross dehydrogenative coupling for c sp3 h heteroarylation mediated by a heterogeneous gan ketone photocatalyst photosensitizer system |
| url | https://doi.org/10.1038/s42004-023-00947-w |
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