Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one

Ignatova, Irina Igorevna; Khoroshilova, Olesya V; Vasilyev, Aleksandr Viktorovich

doi:10.1016/j.mencom.2023.01.008

Home / Publications / Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one

Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one

Irina Igorevna Ignatova ¹

Irina Igorevna Ignatova

,

Olesya V Khoroshilova ¹

Olesya V Khoroshilova

,

Aleksandr Viktorovich Vasilyev ^{1, 2}

Aleksandr Viktorovich Vasilyev

¹ Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation

² St. Petersburg State Forest Tecnical University, St. Petersburg, Russian Federation

10.1016/j.mencom.2023.01.008

Copy DOI

Published 2022-12-26

Communication , Volume 33, Issue 1, 27-29

View PDF

Supporting information

Graphical abstract

3

Share

Cite this

GOST

|

Cite this

GOST Copy

Ignatova I. I., Khoroshilova O. V., Vasilyev A. V. Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 27-29.

GOST all authors (up to 50) Copy

Ignatova I. I., Khoroshilova O. V., Vasilyev A. V. Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 27-29.

RIS

|

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.mencom.2023.01.008

UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.008

TI - Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one

T2 - Mendeleev Communications

AU - Ignatova, Irina Igorevna

AU - Khoroshilova, Olesya V

AU - Vasilyev, Aleksandr Viktorovich

PY - 2022

DA - 2022/12/26

PB - Mendeleev Communications

SP - 27-29

IS - 1

VL - 33

ER -

BibTex

|

Cite this

BibTex (up to 50 authors) Copy

@article{2022_Ignatova,

author = {Irina Igorevna Ignatova and Olesya V Khoroshilova and Aleksandr Viktorovich Vasilyev},

title = {Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one},

journal = {Mendeleev Communications},

year = {2022},

volume = {33},

publisher = {Mendeleev Communications},

month = {Dec},

url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.008},

number = {1},

pages = {27--29},

doi = {10.1016/j.mencom.2023.01.008}

}

MLA

Cite this

MLA Copy

Ignatova, Irina Igorevna, et al. “Aluminium trichloride-promoted tandem hydroarylation-ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 27-29. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.008.

Views

1

Keywords

arylpropynoic acids

carbocations.

hydroarylation

ionic hydrogenation

superelectrophilic activation

ynones

Abstract

Reactions of 3-arylpropynoic acid derivatives and conjugated acetylene ketones with arenes and cyclohexane under the action of AlCl3 at room temperature for 15 h afford the corresponding products of one-pot tandem hydroarylation-ionic hydrogenation of the acetylene bond of the starting compounds in 42-98% yields. This reaction is accompanied by aryl group exchange process under acidic conditions.

References

.

10.1070/RCR4916

Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part I

Beletskaya I.P., Nájera C., Yus M.

Russian Chemical Reviews, 2020

.

10.1016/j.tet.2014.11.033

Tandem superelectrophilic hydroarylation of C C 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.

Tetrahedron, 2015

.

10.1021/acs.joc.6b00419

Friedel–Crafts Alkylation of Arenes with 2-Halogeno-2-CF3-styrenes under Superacidic Conditions. Access to Trifluoromethylated Ethanes and Ethenes

Sandzhieva M.A., Kazakova A.N., Boyarskaya I.A., Ivanov A.Y., Nenajdenko V.G., Vasilyev A.V.

Journal of Organic Chemistry, 2016

.

10.1002/chem.201404139

Gallium-Assisted Transfer Hydrogenation of Alkenes

Michelet B., Bour C., Gandon V.

Chemistry - A European Journal, 2014

.

10.1007/s10593-021-03015-0

Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species

Borisova M.А., Ryabukhin D.S., Ivanov A.Y., Boyarskaya I.A., Spiridonova D.V., Kompanets M.O., Vasilyev A.V.

Chemistry of Heterocyclic Compounds, 2021

.

10.1002/ejoc.200400313

Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions

Koltunov K., Walspurger S., Sommer J.

European Journal of Organic Chemistry, 2004

.

10.1021/jo020099n

Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids.

Koltunov K.Y., Prakash G.K., Rasul G., Olah G.A.

Journal of Organic Chemistry, 2002

.

10.1016/j.tet.2020.131264

Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones

Gorbunova Y., Zakusilo D.N., Boyarskaya I.A., Vasilyev A.V.

Tetrahedron, 2020

.

10.1016/j.tetlet.2015.09.026

One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation

Nilov D.I., Vasilyev A.V.

Tetrahedron Letters, 2015

.

10.1016/j.molcata.2005.09.034

Selective, C,C-double bond reduction of α,β-unsaturated carbonyl compounds with cyclohexane using zeolites

Koltunov K.Y., Walspurger S., Sommer J.

Journal of Molecular Catalysis A Chemical, 2006

.

10.1021/jo0204855

Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions¹

Koltunov K.Y., Prakash G.K., Rasul G., Olah G.A.

Journal of Organic Chemistry, 2002

.

10.1021/jo070875x

Superacidic Activation of Quinoline and Isoquinoline; Their Reactions with Cyclohexane and Benzene¹

Koltunov K.Y., Prakash G.K., Rasul G., Olah G.A.

Journal of Organic Chemistry, 2007

.

10.1039/d2nj01828d

Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species

Kochurin M.A., Ismagilova A.R., Zakusilo D.N., Khoroshilova O.V., Boyarskaya I.A., Vasilyev A.V.

New Journal of Chemistry, 2022

.

10.1007/s00214-018-2312-2

Mechanism of the ethanol-based (C2H5OH2)+(SbF6)− salt formation by the superacid-catalyzed acetaldehyde hydrogenation

Rybacka O., Skurski P.

Theoretical Chemistry Accounts, 2018

.

10.1007/s10562-004-7919-3

Superacid and H-Zeolite Mediated Reactions of Benzaldehyde with Aromatic Compounds and Cyclohexane. The Role of Mono- and Dicationic Intermediates

Koltunov K.Y., Walspurger S., Sommer J.

Catalysis Letters, 2004

.

10.1023/a:1016306814374

Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles

Koltunov K.Y., Repinskaya I.B.

Russian Journal of Organic Chemistry, 2002

.

10.1023/a:1013891616553

Ionic Hydrogenation of α,β-Unsaturated Ketones with Cyclohexane in the Presence of Aluminum Halides

Koltunov K.Y., Repinskaya I.B., Borodkin G.I.

Russian Journal of Organic Chemistry, 2001

.

10.1002/ejoc.200600486

Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes

Koltunov K.Y., Prakash G.K., Rasul G., Olah G.A.

European Journal of Organic Chemistry, 2006

.

10.1016/j.tetlet.2015.03.059

Reactions of 2,3-naphthalenediol with cyclohexane in the presence of aluminum halides

Zhu Z., Ostashevskaya L.A., Koltunov K.Y.

Tetrahedron Letters, 2015

.

10.1016/j.mencom.2020.03.020

Ionic hydrogenation of naphthyl tetrafluoropyridin-4-yl ethers as a new route to 5,6,7,8-tetrahydronaphthols

Zhu Z., Koltunov K.Y.

Mendeleev Communications, 2020

.

10.1016/j.jfluchem.2006.09.008

Reactivity of Vinca alkaloids in superacid

Jacquesy J.

Journal of Fluorine Chemistry, 2006

.

10.1016/j.tetlet.2007.06.023

Superacidic and HUSY-zeolite activation of 1,3-indandione: reactions with benzene and cyclohexane

Koltunov K.Y.

Tetrahedron Letters, 2007

.

10.1016/s0040-4039(01)92183-5

Milieux hyperacides XII - reduction d'enones (1)

Jacquesy J., Jacquesy R., Joly G.

Tetrahedron Letters, 1974

.

10.1016/s0040-4039(98)01889-9

Stereoselective ionic hydrogenation of Vinca alkaloids and vinorelbine in superacids: an access to 4′R-reduced analogs

Lafitte C., Jouannetaud M., Jacquesy J., Fahy J., Duflos A.

Tetrahedron Letters, 1998

.

10.1016/S0040-4020(02)00512-4

Superacid catalyzed reactions of 5-amino-1-naphthol with benzene and cyclohexane

Koltunov K.Y., Surya Prakash G.K., Rasul G., Olah G.A.

Tetrahedron, 2002