Gold(I)-Catalyzed Benzylic C(sp3 )-H Functionalizations : Divergent Synthesis of Indole[a]- and [b]-Fused Polycycles
© 2022 Wiley-VCH GmbH..
Phenyl azides substituted by an (alkylphenyl)ethynyl group facilitate benzylic sp3 (C-H) functionalization in the presence of a JohnPhosAu catalyst, resulting in indole-fused tetra- and pentacycles via divergent N- or C-cyclization. The chemoselectivity is influenced depending on the counter-anion, the electron density of the α-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation originating from a 1,5-hydride shift. An isotopic labeling experiment demonstrates the involvement of an indolylgold(I) species resulting from a tautomerization that is much faster than the deauration. The formation of a benzylic sp3 (C-H) functionalization leading to an indole-fused seven-membered ring is also demonstrated.
| 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), 3 vom: 16. Jan., Seite e202213653 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Greiner, Luca C [VerfasserIn] |
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| Links: |
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| Themen: |
C−H Bond Functionalization |
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| Anmerkungen: |
Date Completed 10.01.2023 Date Revised 11.01.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202213653 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM347700225 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2022 Wiley-VCH GmbH. | ||
| 520 | |a Phenyl azides substituted by an (alkylphenyl)ethynyl group facilitate benzylic sp3 (C-H) functionalization in the presence of a JohnPhosAu catalyst, resulting in indole-fused tetra- and pentacycles via divergent N- or C-cyclization. The chemoselectivity is influenced depending on the counter-anion, the electron density of the α-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation originating from a 1,5-hydride shift. An isotopic labeling experiment demonstrates the involvement of an indolylgold(I) species resulting from a tautomerization that is much faster than the deauration. The formation of a benzylic sp3 (C-H) functionalization leading to an indole-fused seven-membered ring is also demonstrated | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Carbenes | |
| 650 | 4 | |a C−H Bond Functionalization | |
| 650 | 4 | |a Fused Indoles | |
| 650 | 4 | |a Gold Catalysis | |
| 650 | 4 | |a Hydride Shift | |
| 700 | 1 | |a Arichi, Norihito |e verfasserin |4 aut | |
| 700 | 1 | |a Inuki, Shinsuke |e verfasserin |4 aut | |
| 700 | 1 | |a Ohno, Hiroaki |e verfasserin |4 aut | |
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