Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones
Stabilized arylzinc iodides, synthesized by direct insertion of zinc into the corresponding halides, were used as nucleophiles into an acylative Negishi coupling reaction to synthesize chalcones. The reaction conditions were optimized to afford optimal results on a model reaction and then applied to...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-04-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/3/2/6 |
| _version_ | 1797483528678539264 |
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| author | Michele Pierigé Anna Iuliano Gaetano Angelici Gianluca Casotti |
| author_facet | Michele Pierigé Anna Iuliano Gaetano Angelici Gianluca Casotti |
| author_sort | Michele Pierigé |
| collection | DOAJ |
| description | Stabilized arylzinc iodides, synthesized by direct insertion of zinc into the corresponding halides, were used as nucleophiles into an acylative Negishi coupling reaction to synthesize chalcones. The reaction conditions were optimized to afford optimal results on a model reaction and then applied to synthesize nine compounds. Esters, chlorides, electron-rich, electron-poor and sterically hindered substrates are well tolerated and even heteroaryl derivatives can be synthesized. |
| first_indexed | 2024-03-09T22:49:21Z |
| format | Article |
| id | doaj.art-564d63daac15462e90a8ef4d79f9dfb3 |
| institution | Directory Open Access Journal |
| issn | 2673-401X |
| language | English |
| last_indexed | 2024-03-09T22:49:21Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj.art-564d63daac15462e90a8ef4d79f9dfb32023-11-23T18:23:43ZengMDPI AGOrganics2673-401X2022-04-0132879410.3390/org3020006Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of ChalconesMichele Pierigé0Anna Iuliano1Gaetano Angelici2Gianluca Casotti3Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124 Pisa, ItalyDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi, 13, 56124 Pisa, ItalyStabilized arylzinc iodides, synthesized by direct insertion of zinc into the corresponding halides, were used as nucleophiles into an acylative Negishi coupling reaction to synthesize chalcones. The reaction conditions were optimized to afford optimal results on a model reaction and then applied to synthesize nine compounds. Esters, chlorides, electron-rich, electron-poor and sterically hindered substrates are well tolerated and even heteroaryl derivatives can be synthesized.https://www.mdpi.com/2673-401X/3/2/6chalconesorganozinc halidesNegishi couplingcross-couplingacylative cross-couplingarylzinc halides |
| spellingShingle | Michele Pierigé Anna Iuliano Gaetano Angelici Gianluca Casotti Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones Organics chalcones organozinc halides Negishi coupling cross-coupling acylative cross-coupling arylzinc halides |
| title | Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones |
| title_full | Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones |
| title_fullStr | Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones |
| title_full_unstemmed | Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones |
| title_short | Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones |
| title_sort | stabilized arylzinc iodides in negishi acylative cross coupling a modular synthesis of chalcones |
| topic | chalcones organozinc halides Negishi coupling cross-coupling acylative cross-coupling arylzinc halides |
| url | https://www.mdpi.com/2673-401X/3/2/6 |
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