Visible-light-promoted three-component cycloaddition reaction: synthesis of 4-functionalized 1,5-disubstituted 1,2,3-triazoles

被引：8

作者：

Kumar, Atul ^{[1
]}

Kumar, Navaneet ^{[1
,2
]}

Bhadoria, Deepak ^{[1
,2
]}

机构：

[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Sitapur Rd,POB 173 Lucknow, Lucknow 226031, Uttar Pradesh, India

[2] Acad Sci & Innovat Res, Ghaziabad 201002, India

来源：

GREEN CHEMISTRY | 2021年 / 23卷 / 20期

关键词：

AZIDE-ALKYNE CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CATALYZED CYCLOADDITION; TERMINAL ALKYNES; DIRECT ACCESS; IODINE; CYCLIZATION; SULFONES;

D O I：

10.1039/d1gc02328d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. Notably, the reaction proceeds seamlessly without using any transition-metal catalysts, ligands, or photocatalysts, and also reduces chemical waste. It also features an easy operation procedure, high regioselectivity, scalability, a broad substrate scope, mild reaction conditions, and good functional group tolerance.

引用

页码：7987 / 7995

页数：9

共 50 条

[31] Nickel-Catalyzed Azide-Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
Kim, Woo Gyum
Kang, Mi Eun
Lee, Jae Bin
Jeon, Min Ho
Lee, Sungnin
Lee, Jungha
Cho, Bongseo
Cal, Pedro M. S. D.
Kang, Sebyung
Kee, Jung-Min
Bernardes, Goncalo J. L.
Rohde, Jan-Uwe
Choe, Wonyoung
Hong, Sung You
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (35) : 12121 - 12124
[32] Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited
Krasinski, A
Fokin, VV
Sharpless, KB
ORGANIC LETTERS, 2004, 6 (08) : 1237 - 1240
[33] HFIP-Mediated Synthesis of 4-Aryl-NH-1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazolyl Glycoconjugates
Jaiswal, Manoj K.
Yadav, Mangal S.
Maurya, Shristy
Ansari, Danish
Tiwari, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23): : 17213 - 17227
[34] Ce(OTf)3-Catalyzed [3+2] Cycloaddition of Azides with Nitroolefins: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
Wang, Ying-Chun
Xie, Yu-Yang
Qu, Hong-En
Wang, Heng-Shan
Pan, Ying-Ming
Huang, Fu-Ping
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4463 - 4469
[35] A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
Thomas, Joice
John, Jubi
Parekh, Nikita
Dehaen, Wim
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10155 - 10159
[36] Multi-component reaction for the preparation of 1,5-disubstituted 1,2,3-triazoles by in-situ generation of azides and nickel-catalyzed azide-alkyne cycloaddition
Camberlein, Virgyl
Kraupner, Nicolas
Karroum, Nour Bou
Lipka, Emmanuelle
Deprez-Poulain, Rebecca
Deprez, Benoit
Bosc, Damien
TETRAHEDRON LETTERS, 2021, 73
[37] Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition: Role of Er(OTf)3, ionic liquid and water
Maiuolo, Loredana
Russo, Beatrice
Algieri, Vincenzo
Nardi, Monica
Di Gioia, Maria Luisa
Tallarida, Matteo Antonio
De Nino, Antonio
TETRAHEDRON LETTERS, 2019, 60 (09) : 672 - 674
[38] Synthesis of 1.4-disubstituted 1,2,3-triazoles via a three-component reaction in water in the presence of CuX (X = Cl, I)
Wang, Zhong-Xia
Zhao, Zhi-Gang
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) : 89 - 92
[39] Synthesis of disubstituted 1,2,3-triazoles via copper(I)-catalyzed cycloaddition
Calvin, Marcus I.
Hamill, Brayden D.
Mueller, Joann E.
Schoffstall, Allen M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[40] Base-mediated reaction of vinyl bromides with aryl azides: one-pot synthesis of 1,5-disubstituted 1,2,3-triazoles
Wu, Luyong
Chen, Yuxue
Luo, Jianheng
Sun, Qi
Peng, Mingsheng
Lin, Qiang
TETRAHEDRON LETTERS, 2014, 55 (29) : 3847 - 3850

← 1 2 3 4 5 →