Nickel-Catalyzed Unsymmetrical Bis-Allylation of Alkynes
© 2023 Wiley-VCH GmbH..
The catalytic bis-allylation of alkynes is an important but challenging protocol to construct all-carbon tetra-substituted alkenes. Particularly, the catalytic unsymmetrical bis-allylation of alkynes remains as an underexplored task to date. We herein report an unprecedented unsymmetrical bis-allylation by simultaneously utilizing electrophilic trifluoromethyl alkene and nucleophilic allylboronate as the allylic reagents. With the aid of robust Ni0 /NHC catalysis, valuable skipped trienes can be obtained in high regio- and stereo-selectivities under mild conditions. Mechanistic studies indicate that the reaction may proceed through a β-fluorine elimination of a nickelacycle followed by a transmetalation step with allylboronate. The present method exhibits a good tolerance of various functional groups. Besides, the skipped triene products can undergo an array of elaborate transformations, which highlights the potential applications of this strategy.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 62(2023), 17 vom: 17. Apr., Seite e202300036 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Ying [VerfasserIn] |
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| Links: |
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| Themen: |
Alkyne |
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| Anmerkungen: |
Date Completed 06.04.2023 Date Revised 06.04.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202300036 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM353324345 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a The catalytic bis-allylation of alkynes is an important but challenging protocol to construct all-carbon tetra-substituted alkenes. Particularly, the catalytic unsymmetrical bis-allylation of alkynes remains as an underexplored task to date. We herein report an unprecedented unsymmetrical bis-allylation by simultaneously utilizing electrophilic trifluoromethyl alkene and nucleophilic allylboronate as the allylic reagents. With the aid of robust Ni0 /NHC catalysis, valuable skipped trienes can be obtained in high regio- and stereo-selectivities under mild conditions. Mechanistic studies indicate that the reaction may proceed through a β-fluorine elimination of a nickelacycle followed by a transmetalation step with allylboronate. The present method exhibits a good tolerance of various functional groups. Besides, the skipped triene products can undergo an array of elaborate transformations, which highlights the potential applications of this strategy | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Alkyne | |
| 650 | 4 | |a Gem-Difluoroalkene | |
| 650 | 4 | |a Nickel Catalysis | |
| 650 | 4 | |a Skipped Triene | |
| 650 | 4 | |a Unsymmetrical Bis-Allylation | |
| 700 | 1 | |a Zhang, Wei-Song |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Sa-Na |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Xiao-Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Ji, Ding-Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Qing-An |e verfasserin |4 aut | |
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