Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations
dc.contributor.author | Crowley, Daniel C. | |
dc.contributor.author | Brouder, Thomas A. | |
dc.contributor.author | Kearney, Aoife M. | |
dc.contributor.author | Lynch, Denis | |
dc.contributor.author | Ford, Alan | |
dc.contributor.author | Collins, Stuart G. | |
dc.contributor.author | Maguire, Anita R. | |
dc.contributor.funder | Irish Research Council | en |
dc.contributor.funder | Science Foundation Ireland | en |
dc.contributor.funder | European Regional Development Fund | en |
dc.date.accessioned | 2021-08-12T07:52:46Z | |
dc.date.available | 2021-08-12T07:52:46Z | |
dc.date.issued | 2021-08-11 | |
dc.date.updated | 2021-08-12T07:36:45Z | |
dc.description.abstract | Generation and use of triflyl azide in flow enables efficient synthesis of a range of α-diazocarbonyl compounds, including α-diazoketones, α-diazoamides, and an α-diazosulfonyl ester, via both Regitz-type diazo transfer and deacylative/debenzoylative diazo-transfer processes with excellent yields and offers versatility in the solvent employed, in addition to addressing the hazards associated with handling of this highly reactive sulfonyl azide. Telescoping the generation of triflyl azide and diazo-transfer process with highly enantioselective copper-mediated intramolecular aromatic addition and C–H insertion processes demonstrates that the reaction stream containing the α-diazocarbonyl compound can be obtained in sufficient purity to pass directly over the immobilized copper bis(oxazoline) catalyst without detrimentally impacting the catalyst enantioselectivity. | en |
dc.description.sponsorship | Irish Research Council (GOIPG/2015/2972; GOIPG/2015/3188; GOIPG/2018/112); Science Foundation Ireland (SFI SSPC2 12/RC/22755 and SFI SSPC3 Pharm5 12/RC/2275_2; SFI 15/RI/3221) | en |
dc.description.status | Peer reviewed | en |
dc.description.version | Published Version | en |
dc.format.mimetype | application/pdf | en |
dc.identifier.citation | Crowley, D. C., Brouder, T. A., Kearney, A. M., Lynch, D., Ford, A., Collins, S. G. and Maguire, A. R. (2021) 'Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations', Journal of Organic Chemistry. doi: 10.1021/acs.joc.1c01310 | en |
dc.identifier.doi | 10.1021/acs.joc.1c01310 | en |
dc.identifier.eissn | 1520-6904 | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.journaltitle | Journal of Organic Chemistry | en |
dc.identifier.uri | https://hdl.handle.net/10468/11731 | |
dc.language.iso | en | en |
dc.publisher | American Chemical Society | en |
dc.rights | © 2021, the Authors. Published by American Chemical Society. This is an open access article under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). | en |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | en |
dc.subject | Triflyl azide | en |
dc.subject | Regitz-type diazo transfer | en |
dc.subject | Deacylative/debenzoylative diazo transfer | en |
dc.subject | α-diazocarbonyl compounds | en |
dc.subject | α-diazoketones | en |
dc.subject | α-diazoamides | en |
dc.subject | α-diazosulfonyl ester | en |
dc.title | Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations | en |
dc.type | Article (peer-reviewed) | en |
Files
License bundle
1 - 1 of 1
Loading...
- Name:
- license.txt
- Size:
- 2.71 KB
- Format:
- Item-specific license agreed upon to submission
- Description: