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Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase. / Antonov, Alexander S.; Bardakov, Victor G.; Pozharskii, Alexander F.; Vovk, Mikhail A.; Misharev, Alexander D.

In: Journal of Organometallic Chemistry, Vol. 855, 15.01.2018, p. 18-25.

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

Harvard

Antonov, AS, Bardakov, VG, Pozharskii, AF, Vovk, MA & Misharev, AD 2018, 'Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase', Journal of Organometallic Chemistry, vol. 855, pp. 18-25. https://doi.org/10.1016/j.jorganchem.2017.12.007

APA

Antonov, A. S., Bardakov, V. G., Pozharskii, A. F., Vovk, M. A., & Misharev, A. D. (2018). Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase. Journal of Organometallic Chemistry, 855, 18-25. https://doi.org/10.1016/j.jorganchem.2017.12.007

Vancouver

Antonov AS, Bardakov VG, Pozharskii AF, Vovk MA, Misharev AD. Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase. Journal of Organometallic Chemistry. 2018 Jan 15;855:18-25. https://doi.org/10.1016/j.jorganchem.2017.12.007

Author

Antonov, Alexander S. ; Bardakov, Victor G. ; Pozharskii, Alexander F. ; Vovk, Mikhail A. ; Misharev, Alexander D. / Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase. In: Journal of Organometallic Chemistry. 2018 ; Vol. 855. pp. 18-25.

BibTeX

@article{adaa510acca140f8ac18e724623b7fde,
title = "Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase",
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.",
keywords = "Meta-functionalization, Metallation, Organolithium, Proton sponge, METALATION, MECHANISM, ACYLATION, 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE, NMR, LITHIATION, EXCHANGE, DERIVATIVES, CONFORMERS, PERI-NAPHTHYLENEDIAMINES",
author = "Antonov, {Alexander S.} and Bardakov, {Victor G.} and Pozharskii, {Alexander F.} and Vovk, {Mikhail A.} and Misharev, {Alexander D.}",
year = "2018",
month = jan,
day = "15",
doi = "10.1016/j.jorganchem.2017.12.007",
language = "English",
volume = "855",
pages = "18--25",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Laying the way to meta-functionalization of naphthalene proton sponge via the use of Schlosser's superbase

AU - Antonov, Alexander S.

AU - Bardakov, Victor G.

AU - Pozharskii, Alexander F.

AU - Vovk, Mikhail A.

AU - Misharev, Alexander D.

PY - 2018/1/15

Y1 - 2018/1/15

N2 - 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.

AB - 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.

KW - Meta-functionalization

KW - Metallation

KW - Organolithium

KW - Proton sponge

KW - METALATION

KW - MECHANISM

KW - ACYLATION

KW - 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE

KW - NMR

KW - LITHIATION

KW - EXCHANGE

KW - DERIVATIVES

KW - CONFORMERS

KW - PERI-NAPHTHYLENEDIAMINES

UR - http://www.scopus.com/inward/record.url?scp=85038235291&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2017.12.007

DO - 10.1016/j.jorganchem.2017.12.007

M3 - Article

AN - SCOPUS:85038235291

VL - 855

SP - 18

EP - 25

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -

ID: 36561840