Organic Letters

, том 21 , издание 1 , страницы 45-49

Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation

Тип публикации: Journal Article

Дата публикации: 2018-12-18

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b03474

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PubMed ID: 30561214

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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Reported herein is the first example of a gold-catalyzed cyclization of bis(arylmethyl)ethynylphosphine oxides. This represents an original approach to bridgehead methanophosphocines 1, eight-membered heterocycles. Gold catalyst in combination with triflic acid activates alkyne and induces a double hydroarylation. Mechanistic studies suggest that the reaction proceeds stepwise, forming first the 1 H-isophosphinoline 2-oxide 5. Reduction and protection of the corresponding phosphine oxides 1 described herein also highlight the effectiveness of our approach to this new class of electron-rich ligands.

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Газизов Альмир

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161 публикация, 947 цитирований, 23 рецензии

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Институт органической и физической химии им. А.Е. Арбузова КазНЦ РАН

Области научных интересов

Гетероциклические соединения

Органическая химия

Фосфорорганическая химия

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Воронина Юлия

133 публикации, 1 185 цитирований

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Российский экономический университет имени Г. В. Плеханова

Институт общей и неорганической химии им. Н.С. Курнакова РАН

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Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 2, 10% Chemistry of Heterocyclic Compounds 2 публикации, 10%
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Babouri R. et al. Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation // Organic Letters. 2018. Vol. 21. No. 1. pp. 45-49.

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Babouri R., Traore L., Békro Y., Matveeva V. I., Sadykova Y. M., Voronina J. K., Burilov A. R., Ayad T., Volle J. N., Virieux D., Pirat J. Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation // Organic Letters. 2018. Vol. 21. No. 1. pp. 45-49.

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TY - JOUR

DO - 10.1021/acs.orglett.8b03474

UR - https://doi.org/10.1021/acs.orglett.8b03474

TI - Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation

T2 - Organic Letters

AU - Babouri, Rachida

AU - Traore, Lanciné

AU - Békro, Yves-Alain

AU - Matveeva, Victoria I

AU - Sadykova, Yulia M

AU - Voronina, Julia K.

AU - Burilov, Alexander R.

AU - Ayad, Tahar

AU - Volle, Jean Noël

AU - Virieux, David

AU - Pirat, Jean-Luc

PY - 2018

DA - 2018/12/18

PB - American Chemical Society (ACS)

SP - 45-49

IS - 1

VL - 21

PMID - 30561214

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2018_Babouri,

author = {Rachida Babouri and Lanciné Traore and Yves-Alain Békro and Victoria I Matveeva and Yulia M Sadykova and Julia K. Voronina and Alexander R. Burilov and Tahar Ayad and Jean Noël Volle and David Virieux and Jean-Luc Pirat},

title = {Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation},

journal = {Organic Letters},

year = {2018},

volume = {21},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.8b03474},

number = {1},

pages = {45--49},

doi = {10.1021/acs.orglett.8b03474}

}

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Babouri, Rachida, et al. “Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation.” Organic Letters, vol. 21, no. 1, Dec. 2018, pp. 45-49. https://doi.org/10.1021/acs.orglett.8b03474.