dc.contributor.author | Friis, Stig During | |
dc.contributor.author | Pirnot, Michael T | |
dc.contributor.author | Dupuis, Lauren N. | |
dc.contributor.author | Buchwald, Stephen Leffler | |
dc.date.accessioned | 2020-06-30T14:53:46Z | |
dc.date.available | 2020-06-30T14:53:46Z | |
dc.date.issued | 2017-06 | |
dc.identifier.issn | 0570-0833 | |
dc.identifier.uri | https://hdl.handle.net/1721.1/126026 | |
dc.description.abstract | We report an efficient means of sp2-sp3 cross coupling for a variety of terminal monosubstituted olefins with aryl electrophiles using Pd and CuH catalysis. In addition to its applicability to a range of aryl bromide substrates, this process was also suitable for electron-deficient aryl chlorides, furnishing higher yields than the corresponding aryl bromides in these cases. The optimized protocol does not require the use of a glovebox and employs air-stable Cu and Pd complexes as precatalysts. A reaction on 10 mmol scale further highlighted the practical utility of this protocol. Employing a similar protocol, a series of cyclic alkenes were also examined. Cyclopentene was shown to undergo efficient coupling under these conditions. Lastly, deuterium-labeling studies indicate that deuterium scrambling does not take place in this sp2-sp3 cross coupling, implying that β-hydride elimination is not a significant process in this transformation. | en_US |
dc.description.sponsorship | National Institutes of Health (grant no. GM46059) | en_US |
dc.description.sponsorship | National Institutes of Health (postdoctoral fellowship 1F32GM113311) | en_US |
dc.description.sponsorship | Danish Council for Independent Research: Natural Sciences (postdoctoral fellowship 4181-00452). | en_US |
dc.language.iso | en | |
dc.publisher | Wiley | en_US |
dc.relation.isversionof | 10.1002/ANIE.201703400 | en_US |
dc.rights | Creative Commons Attribution-Noncommercial-Share Alike | en_US |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | en_US |
dc.source | PMC | en_US |
dc.title | A dual palladium and copper hydride catalyzed approach for alkyl-aryl cross-coupling of aryl halides and olefins | en_US |
dc.type | Article | en_US |
dc.identifier.citation | Friis, Stig D., et al., "A dual palladium and copper hydride catalyzed approach for alkyl-aryl cross-coupling of aryl halides and olefins." Angewandte Chemie International Edition 56, 25 (June 2017): p. 7242-46 doi 10.1002/ANIE.201703400 ©2017 Author(s) | en_US |
dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
dc.relation.journal | Angewandte Chemie International Edition | en_US |
dc.eprint.version | Author's final manuscript | en_US |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
dc.date.updated | 2019-12-12T18:16:55Z | |
dspace.date.submission | 2019-12-12T18:16:57Z | |
mit.journal.volume | 56 | en_US |
mit.journal.issue | 25 | en_US |
mit.metadata.status | Complete | |