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dc.contributor.authorTasker, Sarah Z.
dc.contributor.authorGutierrez, Alicia C.
dc.contributor.authorJamison, Timothy F.
dc.contributor.authorTasker, Sarah Zinnen
dc.date.accessioned2015-02-19T19:08:30Z
dc.date.available2015-02-19T19:08:30Z
dc.date.issued2014-02
dc.date.submitted2013-11
dc.identifier.issn14337851
dc.identifier.urihttp://hdl.handle.net/1721.1/94650
dc.description.abstractAchieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were able to achieve excellent selectivity for branched products (≥19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to obtaining high branched/linear selectivity, whereas the appropriate base suppressed alkene isomerization of the product. Although aryl triflates are traditionally used to access the cationic Heck pathway, we have shown that, by using triethylsilyl trifluoromethanesulfonate, we can effect a counterion exchange of the catalytic nickel complex, such that cheaper and more stable aryl chlorides, mesylates, tosylates, and sulfamates can be used to yield the same branched products with high selectivity.en_US
dc.description.sponsorshipNational Institute of General Medical Sciences (U.S.) (NIGMS (GM62755))en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (NIH Postdoctoral Fellowship)en_US
dc.description.sponsorshipNational Science Foundation (U.S.) (NSF Graduate Research Fellowship)en_US
dc.language.isoen_US
dc.publisherWiley-VCH Verlag GmbH & Co.en_US
dc.relation.isversionofhttp://dx.doi.org/10.1002/anie.201308391en_US
dc.rightsCreative Commons Attribution-Noncommercial-Share Alikeen_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/en_US
dc.sourcePMCen_US
dc.titleNickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Productsen_US
dc.typeArticleen_US
dc.identifier.citationTasker, Sarah Z., Alicia C. Gutierrez, and Timothy F. Jamison. “Nickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Products.” Angewandte Chemie International Edition 53, no. 7 (January 8, 2014): 1858–1861.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorTasker, Sarah Zinnenen_US
dc.contributor.mitauthorGutierrez, Alicia C.en_US
dc.contributor.mitauthorJamison, Timothy F.en_US
dc.relation.journalAngewandte Chemie International Editionen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsTasker, Sarah Z.; Gutierrez, Alicia C.; Jamison, Timothy F.en_US
dc.identifier.orcidhttps://orcid.org/0000-0003-2315-6983
dc.identifier.orcidhttps://orcid.org/0000-0002-8601-7799
mit.licenseOPEN_ACCESS_POLICYen_US
mit.metadata.statusComplete


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