Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
Publication type: Journal Article
Publication date: 2015-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Cinnamides ArCH CHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1–2 h give C C bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63–98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H–CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
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GOST
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Zakusilo D. N. et al. Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals // Tetrahedron. 2015. Vol. 71. No. 1. pp. 102-108.
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Zakusilo D. N., Ryabukhin D. S., Boyarskaya I. A., Yuzikhin O. S., Vasilyev A. V. Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals // Tetrahedron. 2015. Vol. 71. No. 1. pp. 102-108.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2014.11.033
UR - https://doi.org/10.1016/j.tet.2014.11.033
TI - Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
T2 - Tetrahedron
AU - Zakusilo, Dmitriy N.
AU - Ryabukhin, Dmitry S.
AU - Boyarskaya, Irina A
AU - Yuzikhin, Oleg S
AU - Vasilyev, Aleksander V
PY - 2015
DA - 2015/01/01
PB - Elsevier
SP - 102-108
IS - 1
VL - 71
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2015_Zakusilo,
author = {Dmitriy N. Zakusilo and Dmitry S. Ryabukhin and Irina A Boyarskaya and Oleg S Yuzikhin and Aleksander V Vasilyev},
title = {Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals},
journal = {Tetrahedron},
year = {2015},
volume = {71},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.tet.2014.11.033},
number = {1},
pages = {102--108},
doi = {10.1016/j.tet.2014.11.033}
}
Cite this
MLA
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Zakusilo, Dmitriy N., et al. “Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals.” Tetrahedron, vol. 71, no. 1, Jan. 2015, pp. 102-108. https://doi.org/10.1016/j.tet.2014.11.033.