volume 21 issue 1 pages 45-49

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

Rachida Babouri 1, 2
Lanciné Traore 1, 3
Yves-Alain Békro 3
Victoria I Matveeva 4
Tahar Ayad 5
Jean Noël Volle 1
Jean-Luc Pirat 1
Publication typeJournal Article
Publication date2018-12-18
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.