Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-brom...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/24/7496 |
| _version_ | 1797502213686296576 |
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| author | Shuai Yang Yanghui Zhang |
| author_facet | Shuai Yang Yanghui Zhang |
| author_sort | Shuai Yang |
| collection | DOAJ |
| description | An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C–H functionalization was involved in the reaction. |
| first_indexed | 2024-03-10T03:29:45Z |
| format | Article |
| id | doaj.art-e16b7f5aeb9b454a93e354831140049f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:29:45Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e16b7f5aeb9b454a93e354831140049f2023-11-23T09:45:01ZengMDPI AGMolecules1420-30492021-12-012624749610.3390/molecules26247496Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl BromidesShuai Yang0Yanghui Zhang1Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaShanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaAn expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C–H functionalization was involved in the reaction.https://www.mdpi.com/1420-3049/26/24/7496C–H functionalizationpalladium catalysisspiroindenyl-2-oxindolespalladacyclescascade reaction |
| spellingShingle | Shuai Yang Yanghui Zhang Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides Molecules C–H functionalization palladium catalysis spiroindenyl-2-oxindoles palladacycles cascade reaction |
| title | Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides |
| title_full | Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides |
| title_fullStr | Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides |
| title_full_unstemmed | Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides |
| title_short | Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides |
| title_sort | synthesis of spiroindenyl 2 oxindoles through palladium catalyzed spirocyclization of 2 bromoarylamides and vinyl bromides |
| topic | C–H functionalization palladium catalysis spiroindenyl-2-oxindoles palladacycles cascade reaction |
| url | https://www.mdpi.com/1420-3049/26/24/7496 |
| work_keys_str_mv | AT shuaiyang synthesisofspiroindenyl2oxindolesthroughpalladiumcatalyzedspirocyclizationof2bromoarylamidesandvinylbromides AT yanghuizhang synthesisofspiroindenyl2oxindolesthroughpalladiumcatalyzedspirocyclizationof2bromoarylamidesandvinylbromides |