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Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation

Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Pavel Anatol'evich Volkov 1
Pavel Anatol'evich Volkov
, 
Nina Ivanovna Ivanova 1
Nina Ivanovna Ivanova
, 
Kseniya Olegovna Khrapova 1
Kseniya Olegovna Khrapova
, 
Anton Alekseevich Telezhkin 1
Anton Alekseevich Telezhkin
, 
Alexander Ivanovich Albanov 1
Alexander Ivanovich Albanov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2017.11.004
Published 2017-10-30
Communication , Volume 27, Issue 6, 553-555
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Gusarova N. K. et al. Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 553-555.
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Gusarova N. K., Volkov P. A., Ivanova N. I., Khrapova K. O., Telezhkin A. A., Albanov A. I., Trofimov B. A. Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 553-555.
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TY - JOUR
DO - 10.1016/j.mencom.2017.11.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.004
TI - Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation
T2 - Mendeleev Communications
AU - Gusarova, Nina Kuzminichna
AU - Volkov, Pavel Anatol'evich
AU - Ivanova, Nina Ivanovna
AU - Khrapova, Kseniya Olegovna
AU - Telezhkin, Anton Alekseevich
AU - Albanov, Alexander Ivanovich
AU - Trofimov, Boris Aleksandrovich
PY - 2017
DA - 2017/10/30
PB - Mendeleev Communications
SP - 553-555
IS - 6
VL - 27
ER -
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@article{2017_Gusarova,
author = {Nina Kuzminichna Gusarova and Pavel Anatol'evich Volkov and Nina Ivanovna Ivanova and Kseniya Olegovna Khrapova and Anton Alekseevich Telezhkin and Alexander Ivanovich Albanov and Boris Aleksandrovich Trofimov},
title = {Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.004},
number = {6},
pages = {553--555},
doi = {10.1016/j.mencom.2017.11.004}
}
MLA
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Gusarova, Nina Kuzminichna, et al. “Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation.” Mendeleev Communications, vol. 27, no. 6, Oct. 2017, pp. 553-555. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.004.

Abstract

The non-catalyzed reaction of 2- and 3-substituted pyridines with alkyl propiolates and secondary phosphine chalcogenides (50–52°C, MeCN) produces stereo-, regio- and chemoselectively 1-[(E)-2-(alkoxycarbonyl)ethenyl]-4-chalcogenophosphoryl- 1,4-dihydropyridines in 57–90% yields, the adducts of pyridines with alkyl propiolates being the zwitterionic intermediates. 4-Methylpyridine mainly catalyzes nucleophilic addition of secondary phosphine chalcogenides to alkyl propiolates.

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