Photochemical Michael Addition of Indoles to α,β-Unsaturated Ketones utilizing Arylazo Sulfones as the Photoacid Generators

被引：3

作者：

Galathri, Eirini M. ^{[1
]}

Di Terlizzi, Lorenzo ^{[2
]}

Fagnoni, Maurizio ^{[2
]}

Protti, Stefano ^{[2
]}

Kokotos, Christoforos G. ^{[1
]}

机构：

[1] Natl & Kapodistrian Univ Athens, Dept Chem, Lab Organ Chem, Athens 15771, Greece

[2] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy

来源：

CHEMCATCHEM | 2024年 / 16卷 / 18期

关键词：

photoacid generators (PAGs); photochemistry; Michael addition; alpha; beta-unsaturated ketones; arylazo sulfones; FRIEDEL-CRAFTS ALKYLATION; CATALYZED CONJUGATE ADDITION; IONIC LIQUID; HETEROGENEOUS CATALYST; ACIDS; HYDROACYLATION; LACTONES; WATER;

D O I：

10.1002/cctc.202400686

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The Michael-type addition of indoles represents one of the most important C-C bonds forming reactions at their C-3 position. Herein, we present a mild, versatile and sustainable protocol for the efficient preparation of beta-indolylketones via a Michael addition between indoles and chalcones or alpha,beta-unsaturated ketones in the presence of substituted arylazo sulfones as photoacid generators (PAGs).

引用

页数：5

共 85 条

[1] SnCl2•2H2O -: An alternative to Lewis acidic ionic liquids [J].

Arumugam, Pandurangan ;

Perumal, Paramasivan T. .

CHEMISTRY LETTERS, 2006, 35 (06) :632-633

[2] Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water [J].

Azizi, Najmedin ;

Arynasab, Fezzeh ;

Saidi, Mohammad R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4275-4277

[3] Light-promoted oxidation of aldehydes to carboxylic acids under aerobic and photocatalyst-free conditions [J].

Batsika, Charikleia S. ;

Koutsilieris, Charalampos ;

Koutoulogenis, Giorgos S. ;

Kokotou, Maroula G. ;

Kokotos, Christoforos G. ;

Kokotos, George .

GREEN CHEMISTRY, 2022, 24 (16) :6224-6231

[4] Saturated Oxo Fatty Acids (SOFAs): A Previously Unrecognized Class of Endogenous Bioactive Lipids Exhibiting a Cell Growth Inhibitory Activity [J].

Batsika, Charikleia S. ;

Mantzourani, Christiana ;

Gkikas, Dimitrios ;

Kokotou, Maroula G. ;

Mountanea, Olga G. ;

Kokotos, Christoforos G. ;

Politis, Panagiotis K. ;

Kokotos, George .

JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (09) :5654-5666

[5] Alum (KAI(SO4)2•12H2O) - An Eco-friendly and Versatile Acid-catalyst in Organic Transformations: A Recent Update [J].

Brahmachari, Goutam ;

Nurjamal, Khondekar ;

Begam, Sanchari ;

Mandal, Mullicka ;

Nayek, Nayana ;

Karmakar, Indrajit ;

Mandal, Bhagirath .

CURRENT GREEN CHEMISTRY, 2019, 6 (01) :12-31

[6] THE PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF 2-BROMO-ARYLMERCURY COMPOUNDS AND 2-BROMO-ARYL IODIDES WITH ALPHA,BETA-ENONES - A NEW ENTRY TO 1-INDANOLS [J].

CACCHI, S ;

PALMIERI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 282 (01) :C3-C6

[7] Quaternary Phosphonium Salts as Active Bronsted Acid Catalysts for Friedel-Crafts Reactions [J].

Chen, Lin ;

Xiao, Ben-Xian ;

Du, Wei ;

Chen, Ying-Chun .

ORGANIC LETTERS, 2019, 21 (14) :5733-5736

[8] Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration [J].

Cipagauta Esquivel, Edna Carolina ;

Rufino, Virginia Camila ;

Trindade Nogueira, Matheus Henrique ;

Carbonaro Souza, Ana Carolina ;

Pliego Junior, Josefredo Rodriguez ;

Valle, Marcelo Siqueira .

JOURNAL OF MOLECULAR STRUCTURE, 2020, 1204

[9] Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst [J].

Constantinou, Constantinos T. ;

Gkizis, Petros L. ;

Lagopanagiotopoulou, Olga Thomais G. ;

Skolia, Elpida ;

Nikitas, Nikolaos F. ;

Triandafillidi, Ierasia ;

Kokotos, Christoforos G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (45)

[10] Vanadium(III) chloride (VCl3):: Efficient reagent for the introduction of tetrahydrofuran-based acetal protecting groups for alcohols [J].

Das, Biswanath ;

Krishnaiah, Maddeboina ;

Reddy, Vtukuri Saidi ;

Laxminarayana, Keetha .

HELVETICA CHIMICA ACTA, 2007, 90 (11) :2163-2166

← 1 2 3 4 5 6 7 8 9 →