Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow
An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp[superscript 3])-C(sp[s...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/126090 |
| _version_ | 1826206181976178688 |
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| author | Li, Hui Breen, Christopher P. Seo, Hyowon Jamison, Timothy F Fang, Yuan-Qing Bio, Matthew M. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Li, Hui Breen, Christopher P. Seo, Hyowon Jamison, Timothy F Fang, Yuan-Qing Bio, Matthew M. |
| author_sort | Li, Hui |
| collection | MIT |
| description | An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp[superscript 3])-C(sp[superscript 2]) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process. |
| first_indexed | 2024-09-23T13:25:24Z |
| format | Article |
| id | mit-1721.1/126090 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T13:25:24Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1260902022-10-01T15:12:29Z Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow Li, Hui Breen, Christopher P. Seo, Hyowon Jamison, Timothy F Fang, Yuan-Qing Bio, Matthew M. Massachusetts Institute of Technology. Department of Chemistry Massachusetts Institute of Technology. Department of Chemical Engineering An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp[superscript 3])-C(sp[superscript 2]) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process. NSF (grant no. 164576) 2020-07-08T19:06:59Z 2020-07-08T19:06:59Z 2018-03 2019-12-18T17:22:02Z Article http://purl.org/eprint/type/JournalArticle 1523-7052 https://hdl.handle.net/1721.1/126090 Li, Hui, et al. "Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow." Organic Letters 20, 5 (Mar. 2018): p. 1338-41 doi 10.1021/ACS.ORGLETT.8B00070 ©2018 Author(s) en 10.1021/ACS.ORGLETT.8B00070 Organic Letters Creative Commons Attribution 4.0 International license https://creativecommons.org/licenses/by/4.0/ application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Li, Hui Breen, Christopher P. Seo, Hyowon Jamison, Timothy F Fang, Yuan-Qing Bio, Matthew M. Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title | Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title_full | Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title_fullStr | Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title_full_unstemmed | Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title_short | Ni-catalyzed electrochemical decarboxylative C-C couplings in batch and continuous flow |
| title_sort | ni catalyzed electrochemical decarboxylative c c couplings in batch and continuous flow |
| url | https://hdl.handle.net/1721.1/126090 |
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