Cobalt-Catalyzed (E)-β-Selective Hydrogermylation of Terminal Alkynes
A cobalt-catalyzed method for the hydrogermylation of alkynes is reported, providing a selective and accessible route to (E)-β-vinyl(trialkyl)germanes from terminal alkynes and HGeBu3. As shown in multiple examples, the developed method demonstrates a broad functional group tolerance an practical utility for late-stage hydrogermylation of natural products. The method is compatible with alkynes bearing both aryl and alkyl substituents, providing unrivaled selectivity for previously challenging 1° alkyl-substituted alkynes. Moreover, the catalyst used in this method, Co2(CO)8, is a cheap and commercially available reagent. Conducted mechanistic studies supported the syn-addition of Bu3GeH to an alkyne π-complex.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Organic letters - 23(2021), 8 vom: 16. Apr., Seite 3221-3226 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Radzhabov, Maxim R [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 16.06.2021 Date Revised 16.06.2021 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.1c00928 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM323779743 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A cobalt-catalyzed method for the hydrogermylation of alkynes is reported, providing a selective and accessible route to (E)-β-vinyl(trialkyl)germanes from terminal alkynes and HGeBu3. As shown in multiple examples, the developed method demonstrates a broad functional group tolerance an practical utility for late-stage hydrogermylation of natural products. The method is compatible with alkynes bearing both aryl and alkyl substituents, providing unrivaled selectivity for previously challenging 1° alkyl-substituted alkynes. Moreover, the catalyst used in this method, Co2(CO)8, is a cheap and commercially available reagent. Conducted mechanistic studies supported the syn-addition of Bu3GeH to an alkyne π-complex | ||
| 650 | 4 | |a Journal Article | |
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