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dc.contributor.author
Jamalian, Arezu
dc.contributor.author
Rathman, Benjamin
dc.contributor.author
Borosky, Gabriela Leonor
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dc.contributor.author
Laali, Kenneth K.
dc.date.available
2017-12-27T13:18:50Z
dc.date.issued
2014-08
dc.identifier.citation
Borosky, Gabriela Leonor; Rathman, Benjamin; Jamalian, Arezu; Laali, Kenneth K.; Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Brønsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration; Elsevier Science; Applied Catalysis A: General; 486; 8-2014; 1-11
dc.identifier.issn
0926-860X
dc.identifier.uri
http://hdl.handle.net/11336/31618
dc.description.abstract
The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1–2 was also observed with 0.1–0.3 equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5 mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Brønsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science
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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
1,2-Diaryl-Epoxide
dc.subject
Rearrangement to Carbonyl Compounds
dc.subject
Metallic Triflates
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Bronsted Acidic Anionic Liquids
dc.subject
Substituent Effect on Ar Versus H Migration
dc.subject.classification
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
Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Brønsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2017-12-21T16:26:49Z
dc.journal.volume
486
dc.journal.pagination
1-11
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Jamalian, Arezu. University of North Florida; Estados Unidos
dc.description.fil
Fil: Rathman, Benjamin. University of North Florida; Estados Unidos
dc.description.fil
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.description.fil
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
dc.journal.title
Applied Catalysis A: General
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.apcata.2014.08.009
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0926860X14004943
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