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 50 条

[31] MECHANISM OF PHOTOCHEMICAL ALCOHOL ADDITION TO ALPHA,BETA-UNSATURATED KETONES
RAMEY, BJ
GARDNER, PD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (15) : 3949 - &
[32] A rapid and highly efficient Michael addition of methoxybenzenes and indoles to α,β-unsaturated ketones using BF3•OEt2 as a catalyst
Swetha, A.
Reddy, M. Raghavender
Babu, B. Madhu
Meshram, H. M.
TETRAHEDRON LETTERS, 2017, 58 (47) : 4427 - 4431
[33] MICHAEL ADDITION OF AROMATIC HETEROCYCLIC-COMPOUNDS TO ALPHA-BETA-UNSATURATED KETONES - 3-OXOALKYLATION OF FURANS, INDOLES AND THIOPHENES
DUJARDIN, G
POIRIER, JM
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1994, 131 (08): : 900 - 909
[34] Phosphonium Ionic Liquid-Catalyzed Michael Addition of Mercaptans to α,β-Unsaturated Ketones
Sarda, Swapnil R.
Jadhav, Wamanrao N.
Shete, Amit S.
Dhopte, Kiran B.
Sadawarte, Sachin M.
Gadge, Prashant J.
Pawar, Rajendra P.
SYNTHETIC COMMUNICATIONS, 2010, 40 (14) : 2178 - 2184
[35] Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst
Rana, Nirmal K.
Unhale, Rajshekhar
Singh, Vinod K.
TETRAHEDRON LETTERS, 2012, 53 (16) : 2121 - 2124
[36] Organocatalytic Enantioselective Aza-Michael Addition of Purine Bases to α,β-Unsaturated Ketones
Wu, Hao
Tian, Zhiqing
Zhang, Lili
Huang, Yaodong
Wang, Yongmei
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2977 - 2984
[37] Magnesium-Catalyzed Asymmetric Thia-Michael Addition to α,β-Unsaturated Ketones
Jaszczewska-Adamczak, Joanna A.
Baczewska, Paulina
Bujok, Robert
Mlynarski, Jacek
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (06) : 1412 - 1421
[38] Cesium Carbonate Catalyzed Aza-Michael Addition of Pyrazole to α,β-Unsaturated Ketones
Yang, Jingya
Ma, Ben
Zhou, Hongyan
Zhan, Baohua
Li, Zheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (01) : 121 - 128
[39] Highly Efficient InBr3 Catalyzed Michael Addition of Indoles to α,β-Unsaturated Esters
Liu Ping
Chen Wei
Ren Kai
Wang Lei
CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (12) : 2399 - 2403
[40] KF-Montmorillonite-catalyzed Michael Addition Reaction of Malononitrile to α,β-Unsaturated Ketones
Shi Daqing
Wu Nan
Zhuang Qiya
CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (01) : 169 - 173

← 1 2 3 4 5 →