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)

Orel Vladimir B ^{1, 2}

Vitkovskaya Nadezhda ¹

Kobychev Vladimir ¹

Trofimov B. A. ²

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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: Journal of Organic Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.8b00071

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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.

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Citations by journals

	1 2
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 25% Journal of Organic Chemistry 2 publications, 25%
Molecules	Molecules, 1, 12.5% Molecules 1 publication, 12.5%
International Journal of Quantum Chemistry	International Journal of Quantum Chemistry, 1, 12.5% International Journal of Quantum Chemistry 1 publication, 12.5%
Doklady Chemistry	Doklady Chemistry, 1, 12.5% Doklady Chemistry 1 publication, 12.5%
Nanoscale Advances	Nanoscale Advances, 1, 12.5% Nanoscale Advances 1 publication, 12.5%
Applied Materials Today	Applied Materials Today, 1, 12.5% Applied Materials Today 1 publication, 12.5%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 12.5% European Journal of Organic Chemistry 1 publication, 12.5%
	1 2

Citations by publishers

	1 2
Wiley	Wiley, 2, 25% Wiley 2 publications, 25%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 25% American Chemical Society (ACS) 2 publications, 25%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 12.5% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 12.5%
Pleiades Publishing	Pleiades Publishing, 1, 12.5% Pleiades Publishing 1 publication, 12.5%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 12.5% Royal Society of Chemistry (RSC) 1 publication, 12.5%
Elsevier	Elsevier, 1, 12.5% Elsevier 1 publication, 12.5%
	1 2

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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.

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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%2Facs.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 - Trofimov, B. A.

AU - Orel, Vladimir B

AU - Vitkovskaya, Nadezhda

AU - Kobychev, Vladimir

PY - 2018

DA - 2018/03/05 00:00:00

PB - American Chemical Society (ACS)

SP - 3719-3726

IS - 7

VL - 83

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex Copy

@article{2018_Orel,

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

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%2Facs.joc.8b00071},

number = {7},

pages = {3719--3726},

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

}

MLA

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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%2Facs.joc.8b00071.

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Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

Quartile SCImago

Quartile WOS

Impact factor

3.6

ISSN

00223263 (Print)
15206904 (Electronic)

Labs

Laboratory of Quantum Chemical Modeling of Molecular Systems

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