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dc.contributor.author
Sha, Sheng Chun
dc.contributor.author
Jiang, Hui
dc.contributor.author
Mao, Jianyou
dc.contributor.author
Bellomo Peraza, Ana Ines
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dc.contributor.author
Jeong, Soo A.
dc.contributor.author
Walsh, Patrick J.
dc.date.available
2018-07-03T21:25:14Z
dc.date.issued
2016-01-03
dc.identifier.citation
Sha, Sheng Chun; Jiang, Hui; Mao, Jianyou; Bellomo Peraza, Ana Ines; Jeong, Soo A.; et al.; Nickel-catalyzed allylic alkylation with diarylmethane pronucleophiles: Reaction development and mechanistic insights; Wiley VCH Verlag; Angewandte Chemie; 55; 3; 3-1-2016; 1070-1074
dc.identifier.issn
1433-7851
dc.identifier.uri
http://hdl.handle.net/11336/51133
dc.description.abstract
Palladium-catalyzed allylic substitution reactions are among the most efficient methods to construct C-C bonds between sp3-hybridized carbon atoms. In contrast, much less work has been done with nickel catalysts, perhaps because of the different mechanisms of the allylic substitution reactions. Palladium catalysts generally undergo substitution by a "soft"-nucleophile pathway, wherein the nucleophile attacks the allyl group externally. Nickel catalysts are usually paired with "hard" nucleophiles, which attack the metal before C-C bond formation. Introduced herein is a rare nickel-based catalyst which promotes substitution with diarylmethane pronucleophiles by the soft-nucleophile pathway. Preliminary studies on the asymmetric allylic alkylation are promising. Just a softy: Contrary to what would be predicted, organosodium nucleophiles derived from diarylmethane pronucleophiles are shown to behave as soft nucleophiles in nickel-catalyzed allylic substitution reactions. This general reaction is demonstrated to proceed through a double inversion pathway. A promising asymmetric version is presented.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley VCH Verlag
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Allylic Compounds
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Asymmetric Catalysis
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Cross-Coupling
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Nickel
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Synthetic Methods
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Otras Ciencias Químicas
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Nickel-catalyzed allylic alkylation with diarylmethane pronucleophiles: Reaction development and mechanistic insights
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-06-22T14:34:06Z
dc.journal.volume
55
dc.journal.number
3
dc.journal.pagination
1070-1074
dc.journal.pais
Alemania
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dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Sha, Sheng Chun. University of Pennsylvania; Estados Unidos
dc.description.fil
Fil: Jiang, Hui. University of Pennsylvania; Estados Unidos
dc.description.fil
Fil: Mao, Jianyou. University of Pennsylvania; Estados Unidos
dc.description.fil
Fil: Bellomo Peraza, Ana Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. University of Pennsylvania; Estados Unidos
dc.description.fil
Fil: Jeong, Soo A.. University of Pennsylvania; Estados Unidos
dc.description.fil
Fil: Walsh, Patrick J.. University of Pennsylvania; Estados Unidos
dc.journal.title
Angewandte Chemie
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/anie.201507494
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201507494
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