Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase
Ilia A. Vovk
2
,
Alexander D Misharev
2
Publication type: Journal Article
Publication date: 2018-01-01
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
Lithiation of 1,8-bis(dimethylamino)naphthalene (DMAN) with Schlosser's superbase (n-BuLi–t-BuOK) in the presence of TMEDA in hexane was examined. It has been shown that, compared with previously studied n-BuLi–TMEDA or t-BuLi–TMEDA mixtures, this reagent provides much more selective meta-lithiation. A variety of 3-substituted and 3,6-disubstituted derivatives of DMAN has been prepared in a good to reasonable yield after quenching the reaction mass with different electrophiles. A possibility of further functionalization of thus introduced meta-substituents to synthesize more complex 3-substituted derivatives of DMAN is also demonstrated.
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Citations from 2024:
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Antonov A. S. et al. Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase // Journal of Organometallic Chemistry. 2018. Vol. 855. pp. 18-25.
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Antonov A. S., Bardakov V. G., Pozharskii A. F., Vovk I. A., Misharev A. D. Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase // Journal of Organometallic Chemistry. 2018. Vol. 855. pp. 18-25.
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TY - JOUR
DO - 10.1016/j.jorganchem.2017.12.007
UR - https://doi.org/10.1016/j.jorganchem.2017.12.007
TI - Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase
T2 - Journal of Organometallic Chemistry
AU - Antonov, Alexander S.
AU - Bardakov, Victor G
AU - Pozharskii, Alexander F.
AU - Vovk, Ilia A.
AU - Misharev, Alexander D
PY - 2018
DA - 2018/01/01
PB - Elsevier
SP - 18-25
VL - 855
SN - 0022-328X
SN - 1872-8561
ER -
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@article{2018_Antonov,
author = {Alexander S. Antonov and Victor G Bardakov and Alexander F. Pozharskii and Ilia A. Vovk and Alexander D Misharev},
title = {Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase},
journal = {Journal of Organometallic Chemistry},
year = {2018},
volume = {855},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.jorganchem.2017.12.007},
pages = {18--25},
doi = {10.1016/j.jorganchem.2017.12.007}
}