TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

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TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF₃-allyl alcohols with arenes into CF₃-indanes. / Zerov, Aleksey V.; Bulova, Anastasia A.; Khoroshilova, Olesya V.; Vasilyev, Aleksander V.

в: Organic Chemistry Frontiers, Том 6, № 18, 21.09.2019, стр. 3264-3268.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{7e51433bd044481b9c8af35615d313d4,

title = "TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes",

abstract = "The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes in good yields (up to 99%). The predominant or exclusive formation of indanes with a trans-configuration of 1,3-diaryl groups has been observed. The reaction proceeds through an intermediate formation of the corresponding mesomeric CF3-allyl cations. A plausible reaction mechanism is discussed.",

keywords = "Aromatic hydrocarbons, Ethers, Allyl alcohols, Intermediate formation, Mesomeric, Reaction mechanism, Trans configuration, Reaction intermediates, TRIFLUOROMETHYLATED ALLYL ALCOHOLS, INDENES, CYCLIZATION",

author = "Zerov, {Aleksey V.} and Bulova, {Anastasia A.} and Khoroshilova, {Olesya V.} and Vasilyev, {Aleksander V.}",

year = "2019",

month = sep,

day = "21",

doi = "10.1039/c9qo00822e",

language = "English",

volume = "6",

pages = "3264--3268",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "18",

}

RIS

TY - JOUR

T1 - TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

AU - Zerov, Aleksey V.

AU - Bulova, Anastasia A.

AU - Khoroshilova, Olesya V.

AU - Vasilyev, Aleksander V.

PY - 2019/9/21

Y1 - 2019/9/21

N2 - The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes in good yields (up to 99%). The predominant or exclusive formation of indanes with a trans-configuration of 1,3-diaryl groups has been observed. The reaction proceeds through an intermediate formation of the corresponding mesomeric CF3-allyl cations. A plausible reaction mechanism is discussed.

AB - The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes in good yields (up to 99%). The predominant or exclusive formation of indanes with a trans-configuration of 1,3-diaryl groups has been observed. The reaction proceeds through an intermediate formation of the corresponding mesomeric CF3-allyl cations. A plausible reaction mechanism is discussed.

KW - Aromatic hydrocarbons

KW - Ethers

KW - Allyl alcohols

KW - Intermediate formation

KW - Mesomeric

KW - Reaction mechanism

KW - Trans configuration

KW - Reaction intermediates

KW - TRIFLUOROMETHYLATED ALLYL ALCOHOLS

KW - INDENES

KW - CYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=85072208646&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/tfohpromoted-transformation-tmsethers-diarylsubstituted-cf3allyl-alcohols-arenes-cf3indanes

U2 - 10.1039/c9qo00822e

DO - 10.1039/c9qo00822e

M3 - Article

AN - SCOPUS:85072208646

VL - 6

SP - 3264

EP - 3268

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 18

ER -

ID: 49830479