Organic Letters

, том 22 , издание 7 , страницы 2611-2614

KOBu^t/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes

Тип публикации: Journal Article

Дата публикации: 2020-03-25

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.0c00564

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PubMed ID: 32208621

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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Several imines, readily derived from aryl methyl ketones and benzylamines, react with acetylene gas in KOBut/DMSO system to afford 2-azadienes stereoselectively. This new C-C bond constructing reaction involves, instead of the expected ethynylation of the C═N bond, the addition of azaallyl anions to the triple bond of acetylene.

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Bidusenko I. A. et al. KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes // Organic Letters. 2020. Vol. 22. No. 7. pp. 2611-2614.

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Bidusenko I. A., Schmidt E. Yu., Protsuk N. I., Ushakov I., Vashchenko A. V., Afonin A., Trofimov B. A. KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes // Organic Letters. 2020. Vol. 22. No. 7. pp. 2611-2614.

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TY - JOUR

DO - 10.1021/acs.orglett.0c00564

UR - https://doi.org/10.1021/acs.orglett.0c00564

TI - KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes

T2 - Organic Letters

AU - Bidusenko, Ivan A

AU - Schmidt, Elena Yu

AU - Protsuk, Nadezhda I

AU - Ushakov, Igor

AU - Vashchenko, Alexander V.

AU - Afonin, A.V.

AU - Trofimov, B. A.

PY - 2020

DA - 2020/03/25

PB - American Chemical Society (ACS)

SP - 2611-2614

IS - 7

VL - 22

PMID - 32208621

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2020_Bidusenko,

author = {Ivan A Bidusenko and Elena Yu Schmidt and Nadezhda I Protsuk and Igor Ushakov and Alexander V. Vashchenko and A.V. Afonin and B. A. Trofimov},

title = {KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes},

journal = {Organic Letters},

year = {2020},

volume = {22},

publisher = {American Chemical Society (ACS)},

month = {mar},

url = {https://doi.org/10.1021/acs.orglett.0c00564},

number = {7},

pages = {2611--2614},

doi = {10.1021/acs.orglett.0c00564}

}

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Bidusenko, Ivan A., et al. “KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes.” Organic Letters, vol. 22, no. 7, Mar. 2020, pp. 2611-2614. https://doi.org/10.1021/acs.orglett.0c00564.