Standard

Sterically facilitated meta-lithiation of arenes, containing electron-donating groups. / Antonov, Alexander S.; Bardakov, Victor G.; Mulloyarova, Valeriia V.

в: Journal of Organometallic Chemistry, Том 906, 121068, 15.01.2020.

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

Harvard

Antonov, AS, Bardakov, VG & Mulloyarova, VV 2020, 'Sterically facilitated meta-lithiation of arenes, containing electron-donating groups', Journal of Organometallic Chemistry, Том. 906, 121068. https://doi.org/10.1016/j.jorganchem.2019.121068

APA

Antonov, A. S., Bardakov, V. G., & Mulloyarova, V. V. (2020). Sterically facilitated meta-lithiation of arenes, containing electron-donating groups. Journal of Organometallic Chemistry, 906, [121068]. https://doi.org/10.1016/j.jorganchem.2019.121068

Vancouver

Antonov AS, Bardakov VG, Mulloyarova VV. Sterically facilitated meta-lithiation of arenes, containing electron-donating groups. Journal of Organometallic Chemistry. 2020 Янв. 15;906. 121068. https://doi.org/10.1016/j.jorganchem.2019.121068

Author

Antonov, Alexander S. ; Bardakov, Victor G. ; Mulloyarova, Valeriia V. / Sterically facilitated meta-lithiation of arenes, containing electron-donating groups. в: Journal of Organometallic Chemistry. 2020 ; Том 906.

BibTeX

@article{ce485504d7b849148b685528c6ae5db1,
title = "Sterically facilitated meta-lithiation of arenes, containing electron-donating groups",
abstract = "The influence of the bulky trimethylsilyl substituent on the selectivity of metallation of dimethylaniline, anisole and 1-dimethylaminonaphthalene is studied. The neighboring SiMe3 group forces dimethylamino and methoxy groups to occupy a conformation with an unshared electron pair turned towards silicon atom. This forced conformation prevents NMe2 and OMe groups from providing the DOM-effect, thus facilitating meta-metallation with the use of bulky LiCKOR. While the inverted NMe2 group completely suppresses ortho-metallation, the less bulky and more electron withdrawing OMe group demonstrates more rotation freedom allowing selective ortho-metallation with smaller reagents such as n-BuLi or tert-BuLi.",
keywords = "Aniline, Lithiation, Silicon, Sterical effect, PROTON SPONGE, METALATION",
author = "Antonov, {Alexander S.} and Bardakov, {Victor G.} and Mulloyarova, {Valeriia V.}",
year = "2020",
month = jan,
day = "15",
doi = "10.1016/j.jorganchem.2019.121068",
language = "English",
volume = "906",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Sterically facilitated meta-lithiation of arenes, containing electron-donating groups

AU - Antonov, Alexander S.

AU - Bardakov, Victor G.

AU - Mulloyarova, Valeriia V.

PY - 2020/1/15

Y1 - 2020/1/15

N2 - The influence of the bulky trimethylsilyl substituent on the selectivity of metallation of dimethylaniline, anisole and 1-dimethylaminonaphthalene is studied. The neighboring SiMe3 group forces dimethylamino and methoxy groups to occupy a conformation with an unshared electron pair turned towards silicon atom. This forced conformation prevents NMe2 and OMe groups from providing the DOM-effect, thus facilitating meta-metallation with the use of bulky LiCKOR. While the inverted NMe2 group completely suppresses ortho-metallation, the less bulky and more electron withdrawing OMe group demonstrates more rotation freedom allowing selective ortho-metallation with smaller reagents such as n-BuLi or tert-BuLi.

AB - The influence of the bulky trimethylsilyl substituent on the selectivity of metallation of dimethylaniline, anisole and 1-dimethylaminonaphthalene is studied. The neighboring SiMe3 group forces dimethylamino and methoxy groups to occupy a conformation with an unshared electron pair turned towards silicon atom. This forced conformation prevents NMe2 and OMe groups from providing the DOM-effect, thus facilitating meta-metallation with the use of bulky LiCKOR. While the inverted NMe2 group completely suppresses ortho-metallation, the less bulky and more electron withdrawing OMe group demonstrates more rotation freedom allowing selective ortho-metallation with smaller reagents such as n-BuLi or tert-BuLi.

KW - Aniline

KW - Lithiation

KW - Silicon

KW - Sterical effect

KW - PROTON SPONGE

KW - METALATION

UR - http://www.scopus.com/inward/record.url?scp=85076007999&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2019.121068

DO - 10.1016/j.jorganchem.2019.121068

M3 - Article

AN - SCOPUS:85076007999

VL - 906

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

M1 - 121068

ER -

ID: 49740558