Journal of Organic Chemistry

, volume 83 , issue 7 , pages 3719-3726

Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K)

Vladimir B Orel ^{1, 2}

Nadezhda Vitkovskaya ¹

Vladimir Kobychev ¹

B. A. Trofimov ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Laboratory of Quantum Chemistry, Irkutsk State University, 1 K. Marks Street, 664003 Irkutsk, Russian Federation |

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation |

Publication type: Journal Article

Publication date: 2018-03-05

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.8b00071

Copy DOI

PubMed ID: 29505724

Organic Chemistry

Abstract

Transition-metal-free C-vinylation of acetone with phenylacetylene catalyzed by superbases MOH/DMSO and tBuOM/DMSO (M = Na, K) has been theoretically evaluated in the B3LYP/6-311++G**//B3LYP/6-31+G* approach to rationalize similarities and differences in activity of the above catalytic systems. The close solvate surroundings of sodium and potassium tert-butoxides have been studied. Formation of tBuOM· nDMSO complexes and their structure and thermodynamic stability are discussed in comparison with similar complexes of alkali-metal hydroxides MOH· nDMSO. Activation barriers of the title reaction in the presence of tBuOM· nDMSO complexes are found to be less than those with MOH· nDMSO complexes participating.

Found

5 citations

Orel V

PhD in Chemistry, associate professor

33 publications, 276 citations, 1 review

h-index: 9

Irkutsk State University

3 citations

Bobkov Alexander

PhD in Chemistry

24 publications, 192 citations

h-index: 7

Irkutsk State University

3 citations

Teplyashin Nikita

8 publications, 5 citations

h-index: 2

Irkutsk State University

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Research interests

Quantum Chemistry

Reaction mechanisms

1 citation

Absalyamov Damir

🥼 🤝

8 publications, 74 citations

h-index: 4

Irkutsk State University

Research interests

Quantum Chemistry

1 citation

Ivanov Andrey

54 publications, 534 citations

h-index: 12

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

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Orel V. B. et al. Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K) // Journal of Organic Chemistry. 2018. Vol. 83. No. 7. pp. 3719-3726.

GOST all authors (up to 50) Copy

Orel V. B., Vitkovskaya N., Kobychev V., Trofimov B. A. Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K) // Journal of Organic Chemistry. 2018. Vol. 83. No. 7. pp. 3719-3726.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.8b00071

UR - https://doi.org/10.1021/acs.joc.8b00071

TI - Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K)

T2 - Journal of Organic Chemistry

AU - Orel, Vladimir B

AU - Vitkovskaya, Nadezhda

AU - Kobychev, Vladimir

AU - Trofimov, B. A.

PY - 2018

DA - 2018/03/05

PB - American Chemical Society (ACS)

SP - 3719-3726

IS - 7

VL - 83

PMID - 29505724

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Orel,

author = {Vladimir B Orel and Nadezhda Vitkovskaya and Vladimir Kobychev and B. A. Trofimov},

title = {Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K)},

journal = {Journal of Organic Chemistry},

year = {2018},

volume = {83},

publisher = {American Chemical Society (ACS)},

month = {mar},

url = {https://doi.org/10.1021/acs.joc.8b00071},

number = {7},

pages = {3719--3726},

doi = {10.1021/acs.joc.8b00071}

}

MLA

Cite this

MLA Copy

Orel, Vladimir B., et al. “Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K).” Journal of Organic Chemistry, vol. 83, no. 7, Mar. 2018, pp. 3719-3726. https://doi.org/10.1021/acs.joc.8b00071.

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)

Labs

Laboratory of Quantum Chemical Modeling of Molecular Systems

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