Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Brønsted acids.

Standard

Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Brønsted acids. / Khoroshilova, Olesya V. ; Vasilyev, Aleksander V. ; Boyarskaya, Irina A. .

In: The Journal of organic chemistry, Vol. 87, No. 23, 12.2022, p. 15845-15862.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{28b4ff5bbf66400ab2cd54548001f9f2,

title = "Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Br{\o}nsted acids.",

abstract = "TMS ethers of CF3-benzyl alcohols (and their heterocyclic analogues) undergo elimination of TMSOH molecule with the formation of α-(trifluoromethyl)styrenes in yields of up to 90% under the action of strong Br{\o}nsted acids TfOH or H2SO4. Under the acidic conditions upon prolongation of the reaction, the α-(trifluoromethyl)styrenes are further dimerized into cis-/trans-1,3-di(trifluoromethyl)indanes in yields of up to 100%. Plausible reaction mechanisms of these electrophilic transformations including the intermediate formation of CF3-benzyl carbocations are discussed.",

author = "Khoroshilova, {Olesya V.} and Vasilyev, {Aleksander V.} and Boyarskaya, {Irina A.}",

note = "Khoroshilova O.V., Boyarskaya I.A., Vasilyev A.V. Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Br{\o}nsted acids. Journal of Organic Chemistry. 2022, V. 87, N. 23, P. 15843-15862.",

year = "2022",

month = dec,

doi = "10.1021/acs.joc.2c01961",

language = "English",

volume = "87",

pages = "15845--15862",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

RIS

TY - JOUR

T1 - Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Brønsted acids.

AU - Khoroshilova, Olesya V.

AU - Vasilyev, Aleksander V.

AU - Boyarskaya, Irina A.

N1 - Khoroshilova O.V., Boyarskaya I.A., Vasilyev A.V. Synthesis of α-(trifluoromethyl)styrenes and 1,3-di(trifluoromethyl)indanes via superelectrophilic activation of TMS-ethers of (trifluoromethyl)benzyl alcohols in Brønsted acids. Journal of Organic Chemistry. 2022, V. 87, N. 23, P. 15843-15862.

PY - 2022/12

Y1 - 2022/12

N2 - TMS ethers of CF3-benzyl alcohols (and their heterocyclic analogues) undergo elimination of TMSOH molecule with the formation of α-(trifluoromethyl)styrenes in yields of up to 90% under the action of strong Brønsted acids TfOH or H2SO4. Under the acidic conditions upon prolongation of the reaction, the α-(trifluoromethyl)styrenes are further dimerized into cis-/trans-1,3-di(trifluoromethyl)indanes in yields of up to 100%. Plausible reaction mechanisms of these electrophilic transformations including the intermediate formation of CF3-benzyl carbocations are discussed.

AB - TMS ethers of CF3-benzyl alcohols (and their heterocyclic analogues) undergo elimination of TMSOH molecule with the formation of α-(trifluoromethyl)styrenes in yields of up to 90% under the action of strong Brønsted acids TfOH or H2SO4. Under the acidic conditions upon prolongation of the reaction, the α-(trifluoromethyl)styrenes are further dimerized into cis-/trans-1,3-di(trifluoromethyl)indanes in yields of up to 100%. Plausible reaction mechanisms of these electrophilic transformations including the intermediate formation of CF3-benzyl carbocations are discussed.

U2 - 10.1021/acs.joc.2c01961

DO - 10.1021/acs.joc.2c01961

M3 - Article

VL - 87

SP - 15845

EP - 15862

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -

ID: 102196123