One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and te...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2021-04-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2020.621545/full |
| _version_ | 1818607550340268032 |
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| author | Fa-Jie Chen Fa-Jie Chen Zhenguo Hua Jianhui Chen Jiajia Chen Daesung Lee Yuanzhi Xia |
| author_facet | Fa-Jie Chen Fa-Jie Chen Zhenguo Hua Jianhui Chen Jiajia Chen Daesung Lee Yuanzhi Xia |
| author_sort | Fa-Jie Chen |
| collection | DOAJ |
| description | Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity. |
| first_indexed | 2024-12-16T14:28:32Z |
| format | Article |
| id | doaj.art-7c4a25160da547469a239299157b1270 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-16T14:28:32Z |
| publishDate | 2021-04-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-7c4a25160da547469a239299157b12702022-12-21T22:28:17ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-04-01810.3389/fchem.2020.621545621545One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and HydrohalogenationFa-Jie Chen0Fa-Jie Chen1Zhenguo Hua2Jianhui Chen3Jiajia Chen4Daesung Lee5Yuanzhi Xia6College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaDepartment of Chemistry, University of Illinois at Chicago, Chicago, IL, United StatesCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaDepartment of Chemistry, University of Illinois at Chicago, Chicago, IL, United StatesCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaHerein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.https://www.frontiersin.org/articles/10.3389/fchem.2020.621545/fullSonogashira couplingone-pot synthesisβ-halovinyl ketonehydrohalogenationynones |
| spellingShingle | Fa-Jie Chen Fa-Jie Chen Zhenguo Hua Jianhui Chen Jiajia Chen Daesung Lee Yuanzhi Xia One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation Frontiers in Chemistry Sonogashira coupling one-pot synthesis β-halovinyl ketone hydrohalogenation ynones |
| title | One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation |
| title_full | One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation |
| title_fullStr | One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation |
| title_full_unstemmed | One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation |
| title_short | One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation |
| title_sort | one pot synthesis of z β halovinyl ketones via the cascade of sonogashira coupling and hydrohalogenation |
| topic | Sonogashira coupling one-pot synthesis β-halovinyl ketone hydrohalogenation ynones |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2020.621545/full |
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