Sterically facilitated meta-lithiation of arenes, containing electron-donating groups
Publication type: Journal Article
Publication date: 2020-01-01
scimago Q3
wos Q2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
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.
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Antonov A. S., Bardakov V. G., Mulloyarova V. V. Sterically facilitated meta-lithiation of arenes, containing electron-donating groups // Journal of Organometallic Chemistry. 2020. Vol. 906. p. 121068.
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Antonov A. S., Bardakov V. G., Mulloyarova V. V. Sterically facilitated meta-lithiation of arenes, containing electron-donating groups // Journal of Organometallic Chemistry. 2020. Vol. 906. p. 121068.
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TY - JOUR
DO - 10.1016/j.jorganchem.2019.121068
UR - https://doi.org/10.1016/j.jorganchem.2019.121068
TI - Sterically facilitated meta-lithiation of arenes, containing electron-donating groups
T2 - Journal of Organometallic Chemistry
AU - Antonov, Alexander S.
AU - Bardakov, Victor G
AU - Mulloyarova, V V
PY - 2020
DA - 2020/01/01
PB - Elsevier
SP - 121068
VL - 906
SN - 0022-328X
SN - 1872-8561
ER -
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@article{2020_Antonov,
author = {Alexander S. Antonov and Victor G Bardakov and V V Mulloyarova},
title = {Sterically facilitated meta-lithiation of arenes, containing electron-donating groups},
journal = {Journal of Organometallic Chemistry},
year = {2020},
volume = {906},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.jorganchem.2019.121068},
pages = {121068},
doi = {10.1016/j.jorganchem.2019.121068}
}