Standard

Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals. / Zakusilo, D.N.; Ryabukhin, D.S.; Boyarskaya, I.A.; Yuzikhin, O.S.; Vasilyev, A.V.

в: Tetrahedron, Том 71, № 1, 2014, стр. 102-108.

Результаты исследований: Научные публикации в периодических изданиях › статья

Harvard

Zakusilo, DN, Ryabukhin, DS, Boyarskaya, IA, Yuzikhin, OS & Vasilyev, AV 2014, 'Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals', Tetrahedron, Том. 71, № 1, стр. 102-108. https://doi.org/10.1016/j.tet.2014.11.033

APA

Zakusilo, D. N., Ryabukhin, D. S., Boyarskaya, I. A., Yuzikhin, O. S., & Vasilyev, A. V. (2014). Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals. Tetrahedron, 71(1), 102-108. https://doi.org/10.1016/j.tet.2014.11.033

Vancouver

Zakusilo DN, Ryabukhin DS, Boyarskaya IA, Yuzikhin OS, Vasilyev AV. Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals. Tetrahedron. 2014;71(1):102-108. https://doi.org/10.1016/j.tet.2014.11.033

Author

Zakusilo, D.N. ; Ryabukhin, D.S. ; Boyarskaya, I.A. ; Yuzikhin, O.S. ; Vasilyev, A.V. / Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals. в: Tetrahedron. 2014 ; Том 71, № 1. стр. 102-108.

BibTeX

@article{8d7cf28fbb0c4fc6bd617445d1afeb73,
title = "Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals",
abstract = "Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC 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.",
keywords = "3,3-Diarylpropylamines, Cinnamides, DFT calculations, Hydroarylation, Superacids",
author = "D.N. Zakusilo and D.S. Ryabukhin and I.A. Boyarskaya and O.S. Yuzikhin and A.V. Vasilyev",
year = "2014",
doi = "10.1016/j.tet.2014.11.033",
language = "English",
volume = "71",
pages = "102--108",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "1",

}

RIS

TY - JOUR

T1 - Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

AU - Zakusilo, D.N.

AU - Ryabukhin, D.S.

AU - Boyarskaya, I.A.

AU - Yuzikhin, O.S.

AU - Vasilyev, A.V.

PY - 2014

Y1 - 2014

N2 - Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC 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.

AB - Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC 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.

KW - 3,3-Diarylpropylamines

KW - Cinnamides

KW - DFT calculations

KW - Hydroarylation

KW - Superacids

U2 - 10.1016/j.tet.2014.11.033

DO - 10.1016/j.tet.2014.11.033

M3 - Article

VL - 71

SP - 102

EP - 108

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 1

ER -

ID: 3973393