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- Publisher Website: 10.1021/ja4058844
- Scopus: eid_2-s2.0-84884196932
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Article: Palladium-catalyzed carbene migratory insertion using conjugated ene-yne-ketones as carbene precursors
Title | Palladium-catalyzed carbene migratory insertion using conjugated ene-yne-ketones as carbene precursors |
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Authors | |
Issue Date | 2013 |
Citation | Journal of the American Chemical Society, 2013, v. 135, n. 36, p. 13502-13511 How to Cite? |
Abstract | Palladium-catalyzed cross-coupling reactions between benzyl, aryl, or allyl bromides and conjugated ene-yne-ketones lead to the formation of 2-alkenyl-substituted furans. This novel coupling reaction involves oxidative addition, alkyne activation-cyclization, palladium carbene migratory insertion, β-hydride elimination, and catalyst regeneration. Palladium (2-furyl)carbene is proposed as the key intermediate, which is supported by DFT calculations. The palladium carbene character of the key intermediate is validated by three aspects, including bond lengths, Wiberg bond order indices, and molecular orbitals, by comparison to those reported for stable palladium carbene species. Computational studies also revealed that the rate-limiting step is ene-yne-ketone cyclization, which leads to the formation of the palladium (2-furyl)carbene, while the subsequent carbene migratory insertion is a facile process with a low energy barrier (<5 kcal/mol). © 2013 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/276486 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Xia, Ying | - |
dc.contributor.author | Qu, Shuanglin | - |
dc.contributor.author | Xiao, Qing | - |
dc.contributor.author | Wang, Zhi Xiang | - |
dc.contributor.author | Qu, Peiyuan | - |
dc.contributor.author | Chen, Li | - |
dc.contributor.author | Liu, Zhen | - |
dc.contributor.author | Tian, Leiming | - |
dc.contributor.author | Huang, Zhongxing | - |
dc.contributor.author | Zhang, Yan | - |
dc.contributor.author | Wang, Jianbo | - |
dc.date.accessioned | 2019-09-18T08:33:45Z | - |
dc.date.available | 2019-09-18T08:33:45Z | - |
dc.date.issued | 2013 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2013, v. 135, n. 36, p. 13502-13511 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276486 | - |
dc.description.abstract | Palladium-catalyzed cross-coupling reactions between benzyl, aryl, or allyl bromides and conjugated ene-yne-ketones lead to the formation of 2-alkenyl-substituted furans. This novel coupling reaction involves oxidative addition, alkyne activation-cyclization, palladium carbene migratory insertion, β-hydride elimination, and catalyst regeneration. Palladium (2-furyl)carbene is proposed as the key intermediate, which is supported by DFT calculations. The palladium carbene character of the key intermediate is validated by three aspects, including bond lengths, Wiberg bond order indices, and molecular orbitals, by comparison to those reported for stable palladium carbene species. Computational studies also revealed that the rate-limiting step is ene-yne-ketone cyclization, which leads to the formation of the palladium (2-furyl)carbene, while the subsequent carbene migratory insertion is a facile process with a low energy barrier (<5 kcal/mol). © 2013 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Palladium-catalyzed carbene migratory insertion using conjugated ene-yne-ketones as carbene precursors | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja4058844 | - |
dc.identifier.scopus | eid_2-s2.0-84884196932 | - |
dc.identifier.volume | 135 | - |
dc.identifier.issue | 36 | - |
dc.identifier.spage | 13502 | - |
dc.identifier.epage | 13511 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:000330163200048 | - |
dc.identifier.issnl | 0002-7863 | - |