Journal of Organic Chemistry

, volume 87 , issue 18 , pages 12182-12195

Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

Oleg I Afanasyev ¹

Fedor S Kliuev ^{1, 2}

Alexey A Tsygankov ¹

Yulia V. Nelyubina ^{1, 3}

Evgenii Gutsul ¹

Valentin V Novikov ^{1, 2}

Denis Chusov ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova St. 28, Moscow 119991, Russian Federation |

National Research University Higher School of Economics, Miasnitskaya Str. 20, Moscow 101000, Russian Federation |

Bauman Moscow State Technical University, Baumanskaya Str., 5, 105005 Moscow, Russia |

Publication type: Journal Article

Publication date: 2022-09-07

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.2c01339

Copy DOI

PubMed ID: 36069733

Organic Chemistry

Abstract

Nowadays, design of the new chiral ligands for organometallic catalysts is often based on the step-by-step increase in their complexity to improve efficiency. Herein we describe that simple in situ addition of the fluoride source to the asymmetric organometallic catalyst can improve not only activity but also enantioselectivity. Bromide-nickel diimine complexes were found to catalyze asymmetric Michael addition in low yields and ee, but activation with fluoride leads to a significant improvement in catalyst performance. The developed approach was applied to prepare several enantioenriched GABA analogues.

Found

2 citations

Chusov Denis

DSc in Chemistry, professor

99 publications, 2 395 citations, 35 reviews

h-index: 25

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

1 citation

Vatsadze Sergey

DSc in Chemistry, professor, professor of the Russian Academy of Sciences

170 publications, 2 107 citations, 9 reviews

h-index: 20

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Supramolecular chemistry

1 citation

Afanasyev Oleg

51 publications, 1 268 citations, 11 reviews

h-index: 13

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Belova Svetlana

27 publications, 278 citations

h-index: 10

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Larionov Vladimir

🥼 🤝

DSc in Chemistry

54 publications, 1 085 citations, 106 reviews

h-index: 18

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Peoples' Friendship University of Russia

Research interests

Asymmetric catalysis

1 citation

Burykina Julia

PhD in Chemistry

51 publications, 1 100 citations, 1 review

h-index: 16

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Medvedev Michael

PhD in Physics and Mathematics, associate professor

85 publications, 2 074 citations, 7 reviews

h-index: 19

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Chaliy Vasiliy

🥼

7 publications, 19 citations

h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Bauman Moscow State Technical University

Research interests

Density functional theory (DFT)

Molecular modeling

1 citation

Dudkin Semyon

🥼

PhD in Chemistry

40 publications, 697 citations, 7 reviews

h-index: 13

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Clathrochelates

Coordination Chemistry

Photodynamic Therapy (PDT)

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GOST |

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GOST Copy

Afanasyev O. I. et al. Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12182-12195.

GOST all authors (up to 50) Copy

Afanasyev O. I., Kliuev F. S., Tsygankov A. A., Nelyubina Y. V., Gutsul E., Novikov V. V., Chusov D. Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12182-12195.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.2c01339

UR - https://doi.org/10.1021/acs.joc.2c01339

TI - Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

T2 - Journal of Organic Chemistry

AU - Afanasyev, Oleg I

AU - Kliuev, Fedor S

AU - Tsygankov, Alexey A

AU - Nelyubina, Yulia V.

AU - Gutsul, Evgenii

AU - Novikov, Valentin V

AU - Chusov, Denis

PY - 2022

DA - 2022/09/07

PB - American Chemical Society (ACS)

SP - 12182-12195

IS - 18

VL - 87

PMID - 36069733

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2022_Afanasyev,

author = {Oleg I Afanasyev and Fedor S Kliuev and Alexey A Tsygankov and Yulia V. Nelyubina and Evgenii Gutsul and Valentin V Novikov and Denis Chusov},

title = {Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins},

journal = {Journal of Organic Chemistry},

year = {2022},

volume = {87},

publisher = {American Chemical Society (ACS)},

month = {sep},

url = {https://doi.org/10.1021/acs.joc.2c01339},

number = {18},

pages = {12182--12195},

doi = {10.1021/acs.joc.2c01339}

}

MLA

Cite this

MLA Copy

Afanasyev, Oleg I., et al. “Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins.” Journal of Organic Chemistry, vol. 87, no. 18, Sep. 2022, pp. 12182-12195. https://doi.org/10.1021/acs.joc.2c01339.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)

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