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

D.N. Zakusilo, D.S. Ryabukhin, I.A. Boyarskaya, O.S. Yuzikhin, A.V. Vasilyev

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13 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)102-108
JournalTetrahedron
Volume71
Issue number1
DOIs
Publication statusPublished - 2014

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Reaction intermediates
Discrete Fourier transforms
Pharmaceutical Preparations
lithium aluminum hydride

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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",
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}

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 -