Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade
Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45–90%). This cascade involves an initial Suzuki–Miy...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2024-12-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.20.273 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1841557370101039104 |
|---|---|
| author | Merve Yence Dilgam Ahmadli Damla Surmeli Umut Mert Karacaoğlu Sujit Pal Yunus Emre Türkmen |
| author_facet | Merve Yence Dilgam Ahmadli Damla Surmeli Umut Mert Karacaoğlu Sujit Pal Yunus Emre Türkmen |
| author_sort | Merve Yence |
| collection | DOAJ |
| description | Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45–90%). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[j]fluoranthenes, which are all structurally relevant to benzo[j]fluoranthene-based fungal natural products. The effectiveness of our strategy was demonstrated via a concise, four-step synthesis of the tetramethoxybenzo[j]fluoranthene derivative 18, which represents a formal total synthesis of the fungal natural product bulgarein. |
| format | Article |
| id | doaj-art-a7a4d3658126439d8358e77a3df778bb |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-a7a4d3658126439d8358e77a3df778bb2025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013290329810.3762/bjoc.20.2731860-5397-20-273Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascadeMerve Yence0Dilgam Ahmadli1Damla Surmeli2Umut Mert Karacaoğlu3Sujit Pal4Yunus Emre Türkmen5Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45–90%). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[j]fluoranthenes, which are all structurally relevant to benzo[j]fluoranthene-based fungal natural products. The effectiveness of our strategy was demonstrated via a concise, four-step synthesis of the tetramethoxybenzo[j]fluoranthene derivative 18, which represents a formal total synthesis of the fungal natural product bulgarein.https://doi.org/10.3762/bjoc.20.273acenaphthylene-fused heteroarenesbenzo[j]fluoranthenesc–h arylationfluoranthenesheterocycles |
| spellingShingle | Merve Yence Dilgam Ahmadli Damla Surmeli Umut Mert Karacaoğlu Sujit Pal Yunus Emre Türkmen Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade Beilstein Journal of Organic Chemistry acenaphthylene-fused heteroarenes benzo[j]fluoranthenes c–h arylation fluoranthenes heterocycles |
| title | Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade |
| title_full | Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade |
| title_fullStr | Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade |
| title_full_unstemmed | Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade |
| title_short | Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade |
| title_sort | synthesis of acenaphthylene fused heteroarenes and polyoxygenated benzo j fluoranthenes via a pd catalyzed suzuki miyaura c h arylation cascade |
| topic | acenaphthylene-fused heteroarenes benzo[j]fluoranthenes c–h arylation fluoranthenes heterocycles |
| url | https://doi.org/10.3762/bjoc.20.273 |
| work_keys_str_mv | AT merveyence synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade AT dilgamahmadli synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade AT damlasurmeli synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade AT umutmertkaracaoglu synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade AT sujitpal synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade AT yunusemreturkmen synthesisofacenaphthylenefusedheteroarenesandpolyoxygenatedbenzojfluoranthenesviaapdcatalyzedsuzukimiyauracharylationcascade |