Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis
Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe...
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| Published in | Organic letters Vol. 23; no. 22; pp. 8942 - 8946 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.11.2021
Amer Chemical Soc |
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| Abstract | Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)–H bonds was demonstrated by a series of experimental and computational studies. |
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| AbstractList | Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp(3))-H bonds was demonstrated by a series of experimental and computational studies. Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)–H bonds was demonstrated by a series of experimental and computational studies. |
| Author | Xu, Peng-Fei Yan, Pen-Ji Zhang, Yi-Fan Xiao, Teng-Fei Xu, Guo-Qiang Hai, Jun Hou, Wen-Tao |
| AuthorAffiliation | State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering Lanzhou University State Key Laboratory of Veterinary Etiological Biology, College of Veterinary Medicine College of Chemistry and Chemical Engineering, Key Laboratory of Hexi Corridor Resources Utilization of Gansu Universities |
| AuthorAffiliation_xml | – name: College of Chemistry and Chemical Engineering, Key Laboratory of Hexi Corridor Resources Utilization of Gansu Universities – name: Lanzhou University – name: State Key Laboratory of Veterinary Etiological Biology, College of Veterinary Medicine – name: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering |
| Author_xml | – sequence: 1 givenname: Teng-Fei surname: Xiao fullname: Xiao, Teng-Fei organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering – sequence: 2 givenname: Yi-Fan surname: Zhang fullname: Zhang, Yi-Fan organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering – sequence: 3 givenname: Wen-Tao surname: Hou fullname: Hou, Wen-Tao organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering – sequence: 4 givenname: Pen-Ji surname: Yan fullname: Yan, Pen-Ji organization: College of Chemistry and Chemical Engineering, Key Laboratory of Hexi Corridor Resources Utilization of Gansu Universities – sequence: 5 givenname: Jun orcidid: 0000-0002-7466-4649 surname: Hai fullname: Hai, Jun organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering – sequence: 6 givenname: Peng-Fei orcidid: 0000-0002-5746-758X surname: Xu fullname: Xu, Peng-Fei email: xupf@lzu.edu.cn organization: Lanzhou University – sequence: 7 givenname: Guo-Qiang orcidid: 0000-0002-9683-4581 surname: Xu fullname: Xu, Guo-Qiang email: gqxu@lzu.edu.cn organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering |
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| Keywords | FUNCTIONALIZATION LIGHT ALKANES AMINES C-H ACTIVATION CYCLIZATION METATHESIS |
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| Snippet | Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis |
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