Metalloamination/Cyclization of Zinc(II) Amides Derived from N,N-Dimethylhydrazinoalkenes—Applications for the Direct C-SP2 Functionalization of Aryl and Vinyl Electrophiles

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dc.contributor.authorLépeule, Jérome
dc.contributor.authorFrabitore, Christian
dc.contributor.authorLivinghouse, Tom
dc.date.accessioned2026-06-12T20:16:29Z
dc.date.issued2025-09
dc.description.abstractTreatment of N,N-dimethylhydrazinoalkenes with diethylzinc followed by exposure of the resulting ethylzinc amides to high vacuum drives a Schlenck redistribution metalloamination/cyclization to generate the corresponding bis(organozinc) intermediates in excellent conversions. Direct treatment of these with appropriate aryl or vinyl electrophiles in the presence of catalytic PdCl2 (DPEphos) provides the corresponding arylated or alkenylated pyrrolidines and piperidines with high efficiency.
dc.identifier.citationLépeule J, Frabitore C, Livinghouse T. Metalloamination/Cyclization of Zinc(II) Amides Derived from N,N-Dimethylhydrazinoalkenes—Applications for the Direct C-SP2 Functionalization of Aryl and Vinyl Electrophiles. Inorganics. 2025; 13(10):328. https://doi.org/10.3390/inorganics13100328
dc.identifier.doi10.3390/inorganics13100328
dc.identifier.issn2304-6740
dc.identifier.urihttps://scholarworks.montana.edu/handle/1/19848
dc.language.isoen_US
dc.publisherMDPI AG
dc.rightscc-by
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectsynthetic methods
dc.subjectpyrrolidine
dc.subjectpalladium catalysis
dc.subjectdialkylzinc
dc.subjectNegishi coupling
dc.titleMetalloamination/Cyclization of Zinc(II) Amides Derived from N,N-Dimethylhydrazinoalkenes—Applications for the Direct C-SP2 Functionalization of Aryl and Vinyl Electrophiles
dc.typeAnimation
mus.citation.extentfirstpage1
mus.citation.extentlastpage9
mus.citation.issue10
mus.citation.journaltitleInorganics
mus.citation.volume13
mus.relation.collegeCollege of Letters & Science
mus.relation.departmentChemistry & Biochemistry
mus.relation.universityMontana State University - Bozeman

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