Noncovalent Li···H Interaction in the Synthesis of peri -Disubstituted Naphthalene Proton Sponges

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Noncovalent Li···H Interaction in the Synthesis of peri -Disubstituted Naphthalene Proton Sponges. / Antonov, Alexander S.; Yakubenko, Artyom A.

In: Synthesis (Germany), Vol. 52, No. 1, ss-2019-n0242-op, 01.01.2020, p. 98-104.

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

BibTeX

@article{5041eeb2101f45cc8555bd6209872f1a,

title = "Noncovalent Li···H Interaction in the Synthesis of peri -Disubstituted Naphthalene Proton Sponges",

abstract = "Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n -BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri -position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.",

keywords = "agostic interaction, lithium, metalation, naphthalene, proton sponge, BASICITY, 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE, 1-NME2 GROUP, LITHIUM, DERIVATIVES, TRANSFORMATIONS, NAPHTHYLENEDIAMINES, WATER",

author = "Antonov, {Alexander S.} and Yakubenko, {Artyom A.}",

year = "2020",

month = jan,

day = "1",

doi = "10.1055/s-0039-1690230",

language = "English",

volume = "52",

pages = "98--104",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "1",

}

RIS

TY - JOUR

T1 - Noncovalent Li···H Interaction in the Synthesis of peri -Disubstituted Naphthalene Proton Sponges

AU - Antonov, Alexander S.

AU - Yakubenko, Artyom A.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n -BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri -position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.

AB - Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n -BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri -position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.

KW - agostic interaction

KW - lithium

KW - metalation

KW - naphthalene

KW - proton sponge

KW - BASICITY

KW - 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE

KW - 1-NME2 GROUP

KW - LITHIUM

KW - DERIVATIVES

KW - TRANSFORMATIONS

KW - NAPHTHYLENEDIAMINES

KW - WATER

UR - http://www.scopus.com/inward/record.url?scp=85076711065&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/2f791802-3099-3092-81ed-474112b2c866/

U2 - 10.1055/s-0039-1690230

DO - 10.1055/s-0039-1690230

M3 - Article

AN - SCOPUS:85076711065

VL - 52

SP - 98

EP - 104

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 1

M1 - ss-2019-n0242-op

ER -

ID: 50057772