Ru(II)-Catalyzed Carboamination of Olefins with α-Carbonyl Sulfoxonium Ylides
The first ruthenium-catalyzed carboamination of olefins with α-carbonyl sulfoxonium ylides is reported. The utilization of an inexpensive ruthenium catalyst enables the concise synthesis of pharmaceutically important isoindolin-1-ones, which possess both a stereogenic center and β-carbonyl side chain. This method is mild, efficient, and scalable and allows for the coupling of a wide range of aryl-, heteroaryl-, alkenyl-, and alkyl-substituted sulfoxonium ylides. Moreover, the carbonyl side chain in the resulting product provides a good handle for downstream transformations. For mechanistic studies, a ruthacyle complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:89 |
|---|---|
| Enthalten in: |
The Journal of organic chemistry - 89(2024), 8 vom: 19. Apr., Seite 5382-5391 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Zhang, Zhenwei [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Revised 19.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.joc.3c02788 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM370462661 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM370462661 | ||
| 003 | DE-627 | ||
| 005 | 20240419232550.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240401s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.joc.3c02788 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1380.xml |
| 035 | |a (DE-627)NLM370462661 | ||
| 035 | |a (NLM)38556754 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Zhang, Zhenwei |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Ru(II)-Catalyzed Carboamination of Olefins with α-Carbonyl Sulfoxonium Ylides |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 19.04.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The first ruthenium-catalyzed carboamination of olefins with α-carbonyl sulfoxonium ylides is reported. The utilization of an inexpensive ruthenium catalyst enables the concise synthesis of pharmaceutically important isoindolin-1-ones, which possess both a stereogenic center and β-carbonyl side chain. This method is mild, efficient, and scalable and allows for the coupling of a wide range of aryl-, heteroaryl-, alkenyl-, and alkyl-substituted sulfoxonium ylides. Moreover, the carbonyl side chain in the resulting product provides a good handle for downstream transformations. For mechanistic studies, a ruthacyle complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Su, Borong |e verfasserin |4 aut | |
| 700 | 1 | |a Zhong, Fuhong |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Yongyan |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Yao |e verfasserin |4 aut | |
| 700 | 1 | |a Mai, Shaoyu |e verfasserin |4 aut | |
| 700 | 1 | |a Tao, Huaming |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t The Journal of organic chemistry |d 1945 |g 89(2024), 8 vom: 19. Apr., Seite 5382-5391 |w (DE-627)NLM000006343 |x 1520-6904 |7 nnns |
| 773 | 1 | 8 | |g volume:89 |g year:2024 |g number:8 |g day:19 |g month:04 |g pages:5382-5391 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.joc.3c02788 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 89 |j 2024 |e 8 |b 19 |c 04 |h 5382-5391 | ||