Site- and Enantioselective Manganese-Catalyzed Benzylic C-H Azidation of Indolines
A manganese-catalyzed highly site- and enantioselective benzylic C-H azidation of indolines has been described. The practical method is applicable for azidation of a tertiary benzylic C-H bond with good functional group tolerance, allowing facile access to structurally diverse tertiary azide-containing indolines in high efficiency with excellent site-, chemo-, and enantioselectivity. The generality of the method was further demonstrated by site- and enantioselective azidation of the secondary benzylic C-H bond for a range of secondary azide-containing indolines. The benzylic C-H azidation method allows to straightforwardly and enantioselectively install a variety of nitrogen-based functional groups and diverse bioactive molecules at the C3 position of indoline frameworks through post-azidation manipulations. Gram-scale synthesis was also demonstrated, further highlighting the synthetic potential of the method. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:144 |
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| Enthalten in: |
Journal of the American Chemical Society - 144(2022), 33 vom: 24. Aug., Seite 15383-15390 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Cao, Min [VerfasserIn] |
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| Links: |
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| Themen: |
42Z2K6ZL8P |
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| Anmerkungen: |
Date Completed 25.08.2022 Date Revised 02.09.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/jacs.2c07089 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM344708896 |
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| 500 | |a Date Revised 02.09.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A manganese-catalyzed highly site- and enantioselective benzylic C-H azidation of indolines has been described. The practical method is applicable for azidation of a tertiary benzylic C-H bond with good functional group tolerance, allowing facile access to structurally diverse tertiary azide-containing indolines in high efficiency with excellent site-, chemo-, and enantioselectivity. The generality of the method was further demonstrated by site- and enantioselective azidation of the secondary benzylic C-H bond for a range of secondary azide-containing indolines. The benzylic C-H azidation method allows to straightforwardly and enantioselectively install a variety of nitrogen-based functional groups and diverse bioactive molecules at the C3 position of indoline frameworks through post-azidation manipulations. Gram-scale synthesis was also demonstrated, further highlighting the synthetic potential of the method. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Azides |2 NLM | |
| 650 | 7 | |a Indoles |2 NLM | |
| 650 | 7 | |a Ions |2 NLM | |
| 650 | 7 | |a Manganese |2 NLM | |
| 650 | 7 | |a 42Z2K6ZL8P |2 NLM | |
| 650 | 7 | |a indoline |2 NLM | |
| 650 | 7 | |a 6DPT9AB2NK |2 NLM | |
| 700 | 1 | |a Wang, Hongliang |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Yingang |e verfasserin |4 aut | |
| 700 | 1 | |a Tung, Chen-Ho |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Lei |e verfasserin |4 aut | |
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