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Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes. / Kazakova, A.N.; Iakovenko, R.O.; Boyarskaya, I.A.; Nenajdenko, V.G.; Vasilyev, A.V.

в: Journal of Organic Chemistry, Том 80, № 19, 2015, стр. 9506-9517.

Результаты исследований: Научные публикации в периодических изданиях › статья

Harvard

Kazakova, AN, Iakovenko, RO, Boyarskaya, IA, Nenajdenko, VG & Vasilyev, AV 2015, 'Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes', Journal of Organic Chemistry, Том. 80, № 19, стр. 9506-9517. https://doi.org/10.1021/acs.joc.5b01398

APA

Kazakova, A. N., Iakovenko, R. O., Boyarskaya, I. A., Nenajdenko, V. G., & Vasilyev, A. V. (2015). Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes. Journal of Organic Chemistry, 80(19), 9506-9517. https://doi.org/10.1021/acs.joc.5b01398

Vancouver

Kazakova AN, Iakovenko RO, Boyarskaya IA, Nenajdenko VG, Vasilyev AV. Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes. Journal of Organic Chemistry. 2015;80(19):9506-9517. https://doi.org/10.1021/acs.joc.5b01398

Author

Kazakova, A.N. ; Iakovenko, R.O. ; Boyarskaya, I.A. ; Nenajdenko, V.G. ; Vasilyev, A.V. / Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes. в: Journal of Organic Chemistry. 2015 ; Том 80, № 19. стр. 9506-9517.

BibTeX

@article{69f87895ec0d4f7383d4b223767e3bfb,
title = "Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes",
abstract = "Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH=CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar′)CHCH=CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.",
keywords = "electrophilic reactions, CF3-allylic alcohols, superacids, fluorine eletrophiles, CF3-alkenes, CF3-indanes, electrophilic aromatic substitution",
author = "A.N. Kazakova and R.O. Iakovenko and I.A. Boyarskaya and V.G. Nenajdenko and A.V. Vasilyev",
year = "2015",
doi = "10.1021/acs.joc.5b01398",
language = "English",
volume = "80",
pages = "9506--9517",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

RIS

TY - JOUR

T1 - Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes

AU - Kazakova, A.N.

AU - Iakovenko, R.O.

AU - Boyarskaya, I.A.

AU - Nenajdenko, V.G.

AU - Vasilyev, A.V.

PY - 2015

Y1 - 2015

N2 - Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH=CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar′)CHCH=CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.

AB - Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH=CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar′)CHCH=CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.

KW - electrophilic reactions

KW - CF3-allylic alcohols

KW - superacids

KW - fluorine eletrophiles

KW - CF3-alkenes

KW - CF3-indanes

KW - electrophilic aromatic substitution

U2 - 10.1021/acs.joc.5b01398

DO - 10.1021/acs.joc.5b01398

M3 - Article

VL - 80

SP - 9506

EP - 9517

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

ID: 3973167