Russian Journal of Organic Chemistry

, том 38 , издание 10 , страницы 1475-1478

Mechanism of catalytic addition of benzeneselenol to alkynes

V P Ananikov ¹

D A Malyshev ¹

I P Beletskaya ²

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Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia |

Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, Russia |

Тип публикации: Journal Article

Дата публикации: 2002-01-01

Pleiades Publishing

Russian Journal of Organic Chemistry

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wos Q4

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SJR: 0.190

CiteScore: 1.3

Impact factor: 0.9

ISSN: 10704280, 16083393

DOI: 10.1023/A:1022500420741

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Organic Chemistry

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Addition of benzeneselenol to terminal alkynes HCÍÄCR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the PdÄSe bond, and reductive elimination.

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Ananikov V. P., Malyshev D. A., Beletskaya I. P. Mechanism of catalytic addition of benzeneselenol to alkynes // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 10. pp. 1475-1478.

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Ananikov V. P., Malyshev D. A., Beletskaya I. P. Mechanism of catalytic addition of benzeneselenol to alkynes // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 10. pp. 1475-1478.

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TY - JOUR

DO - 10.1023/A:1022500420741

UR - https://doi.org/10.1023/A:1022500420741

TI - Mechanism of catalytic addition of benzeneselenol to alkynes

T2 - Russian Journal of Organic Chemistry

AU - Ananikov, V P

AU - Malyshev, D A

AU - Beletskaya, I P

PY - 2002

DA - 2002/01/01

PB - Pleiades Publishing

SP - 1475-1478

IS - 10

VL - 38

SN - 1070-4280

SN - 1608-3393

ER -

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@article{2002_Ananikov,

author = {V P Ananikov and D A Malyshev and I P Beletskaya},

title = {Mechanism of catalytic addition of benzeneselenol to alkynes},

journal = {Russian Journal of Organic Chemistry},

year = {2002},

volume = {38},

publisher = {Pleiades Publishing},

month = {jan},

url = {https://doi.org/10.1023/A:1022500420741},

number = {10},

pages = {1475--1478},

doi = {10.1023/A:1022500420741}

}

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Ananikov, V. P., et al. “Mechanism of catalytic addition of benzeneselenol to alkynes.” Russian Journal of Organic Chemistry, vol. 38, no. 10, Jan. 2002, pp. 1475-1478. https://doi.org/10.1023/A:1022500420741.