Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization
A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addit...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2022-10-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2022.1058596/full |
| _version_ | 1828142544848945152 |
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| author | Shijing Tu Zhongyu Qi Weicai Li Shiqi Zhang Zhijie Zhang Jun Wei Lin Yang Siping Wei Xi Du Dong Yi |
| author_facet | Shijing Tu Zhongyu Qi Weicai Li Shiqi Zhang Zhijie Zhang Jun Wei Lin Yang Siping Wei Xi Du Dong Yi |
| author_sort | Shijing Tu |
| collection | DOAJ |
| description | A chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addition and switchable distal C(sp3)–H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp3)–N bond formation and C(sp3)–C(sp2) bond formation is precisely switched by photocatalysts (Ru(bpy)3(PF6)2 vs. fac-Ir(ppy)3) and additives (base vs. acid). |
| first_indexed | 2024-04-11T19:42:05Z |
| format | Article |
| id | doaj.art-b4f0cda86a524d1599c01d80755e3a06 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-11T19:42:05Z |
| publishDate | 2022-10-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-b4f0cda86a524d1599c01d80755e3a062022-12-22T04:06:40ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462022-10-011010.3389/fchem.2022.10585961058596Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalizationShijing Tu0Zhongyu Qi1Weicai Li2Shiqi Zhang3Zhijie Zhang4Jun Wei5Lin Yang6Siping Wei7Xi Du8Dong Yi9Central Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaNatural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaDepartment of Chemistry, School of Basic Medical Science, Southwest Medical University, Luzhou, ChinaCentral Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, ChinaA chemodivergent photocatalytic approach to 1-pyrrolines and 1-tetralones from alkyl bromides and vinyl azides has been developed through chemoselectively controllable intermolecular [3 + 2] and [4 + 2] cyclization. This photoredox-neutral two-component protocol involves intermolecular radical addition and switchable distal C(sp3)–H functionalization enabled by iminyl radical-mediated 1,5-hydrogen atom transfer. Meanwhile, chemoselectivity between C(sp3)–N bond formation and C(sp3)–C(sp2) bond formation is precisely switched by photocatalysts (Ru(bpy)3(PF6)2 vs. fac-Ir(ppy)3) and additives (base vs. acid).https://www.frontiersin.org/articles/10.3389/fchem.2022.1058596/full1-pyrrolineshydrogen atom transfer[3+2] cyclization[4+2] cyclization1-tetralones |
| spellingShingle | Shijing Tu Zhongyu Qi Weicai Li Shiqi Zhang Zhijie Zhang Jun Wei Lin Yang Siping Wei Xi Du Dong Yi Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization Frontiers in Chemistry 1-pyrrolines hydrogen atom transfer [3+2] cyclization [4+2] cyclization 1-tetralones |
| title | Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization |
| title_full | Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization |
| title_fullStr | Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization |
| title_full_unstemmed | Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization |
| title_short | Chemodivergent photocatalytic access to 1-pyrrolines and 1-tetralones involving switchable C(sp3)–H functionalization |
| title_sort | chemodivergent photocatalytic access to 1 pyrrolines and 1 tetralones involving switchable c sp3 h functionalization |
| topic | 1-pyrrolines hydrogen atom transfer [3+2] cyclization [4+2] cyclization 1-tetralones |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2022.1058596/full |
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