Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles
This journal is © The Royal Society of Chemistry 2019..
The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C-C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon-carbon bonds sequentially.
| Errataetall: |
ErratumIn: Chem Sci. 2020 Jan 10;11(4):1177. - PMID 35414862 |
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| Medienart: |
E-Artikel |
| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:10 |
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| Enthalten in: |
Chemical science - 10(2019), 45 vom: 07. Dez., Seite 10601-10606 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Chen, Jichao [VerfasserIn] |
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Date Revised 13.11.2023 published: Electronic-eCollection ErratumIn: Chem Sci. 2020 Jan 10;11(4):1177. - PMID 35414862 Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/c9sc04122b |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a ErratumIn: Chem Sci. 2020 Jan 10;11(4):1177. - PMID 35414862 | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a This journal is © The Royal Society of Chemistry 2019. | ||
| 520 | |a The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C-C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon-carbon bonds sequentially | ||
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