Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst

Handle URI:
http://hdl.handle.net/10754/626891
Title:
Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst
Authors:
El-Sepelgy, Osama ( 0000-0003-3131-4988 ) ; Brzozowska, Aleksandra; Sklyaruk, Jan; Jang, Yoon Kyung; Zubar, Viktoriia; Rueping, Magnus ( 0000-0003-4580-5227 )
Abstract:
A new iron-catalyzed chemoselective intramolecular hydroamination and hydroalkoxylation of the readily available α-allenic amines and alcohols to valuable unsaturated 5-membered heterocycles, 2,3-dihydropyrrole and 2,3-dihydrofuran, is reported. Effective selectivity control is achieved by a metal–ligand cooperative activation of the substrates. The mild reaction conditions and the use of low amounts of an air and moisture stable iron catalyst allow for the hydrofunctionalization of a wide range of allenes bearing different functional groups in good yields in the absence of base or any sensitive additives.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)
Citation:
El-Sepelgy O, Brzozowska A, Sklyaruk J, Jang YK, Zubar V, et al. (2018) Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst. Organic Letters. Available: http://dx.doi.org/10.1021/acs.orglett.7b03828.
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
Issue Date:
18-Jan-2018
DOI:
10.1021/acs.orglett.7b03828
Type:
Article
ISSN:
1523-7060; 1523-7052
Sponsors:
J.S. thanks FCI for the predoctoral fellowship.
Additional Links:
http://pubs.acs.org/doi/10.1021/acs.orglett.7b03828
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorEl-Sepelgy, Osamaen
dc.contributor.authorBrzozowska, Aleksandraen
dc.contributor.authorSklyaruk, Janen
dc.contributor.authorJang, Yoon Kyungen
dc.contributor.authorZubar, Viktoriiaen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2018-01-28T07:22:28Z-
dc.date.available2018-01-28T07:22:28Z-
dc.date.issued2018-01-18en
dc.identifier.citationEl-Sepelgy O, Brzozowska A, Sklyaruk J, Jang YK, Zubar V, et al. (2018) Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst. Organic Letters. Available: http://dx.doi.org/10.1021/acs.orglett.7b03828.en
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.doi10.1021/acs.orglett.7b03828en
dc.identifier.urihttp://hdl.handle.net/10754/626891-
dc.description.abstractA new iron-catalyzed chemoselective intramolecular hydroamination and hydroalkoxylation of the readily available α-allenic amines and alcohols to valuable unsaturated 5-membered heterocycles, 2,3-dihydropyrrole and 2,3-dihydrofuran, is reported. Effective selectivity control is achieved by a metal–ligand cooperative activation of the substrates. The mild reaction conditions and the use of low amounts of an air and moisture stable iron catalyst allow for the hydrofunctionalization of a wide range of allenes bearing different functional groups in good yields in the absence of base or any sensitive additives.en
dc.description.sponsorshipJ.S. thanks FCI for the predoctoral fellowship.en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/10.1021/acs.orglett.7b03828en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/10.1021/acs.orglett.7b03828.en
dc.titleCooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalysten
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalOrganic Lettersen
dc.eprint.versionPost-printen
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germanyen
kaust.authorRueping, Magnusen
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