Literature DB >> 20309486

Click chemistry under non-classical reaction conditions.

C Oliver Kappe1, Erik Van der Eycken.   

Abstract

First described almost a decade ago, "click" reactions such as the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) are widely used today in organic and medicinal chemistry, in the polymer and material science field, and in chemical biology. While most click reactions can be performed at room temperature there are instances where some form of process intensification is required. In this tutorial review, aimed at the synthetic chemistry community, examples of click chemistry carried out under non-classical reaction conditions, such as for example applying microwave heating or continuous flow processing will be highlighted.

Entities:  

Year:  2009        PMID: 20309486     DOI: 10.1039/b901973c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  28 in total

1.  α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.

Authors:  Krisztina Kónya; Szabolcs Fekete; Anita Abrahám; Tamás Patonay
Journal:  Mol Divers       Date:  2012-02-04       Impact factor: 2.943

2.  Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles.

Authors:  Stanley N S Vasconcelos; Evelin Fornari; Ignez Caracelli; Hélio A Stefani
Journal:  Mol Divers       Date:  2017-07-12       Impact factor: 2.943

3.  Synthesis of carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases.

Authors:  Jong Hyun Cho; Steven J Coats; Raymond F Schinazi
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  One-step continuous flow synthesis of highly substituted pyrrole-3-carboxylic acid derivatives via in situ hydrolysis of tert-butyl esters.

Authors:  Ananda Herath; Nicholas D P Cosford
Journal:  Org Lett       Date:  2010-10-21       Impact factor: 6.005

5.  Rapid grafting of azido-labeled oligo(ethylene glycol)s onto an alkynyl-terminated monolayer on nonoxidized silicon via microwave-assisted "click" reaction.

Authors:  Yan Li; Jun Wang; Chengzhi Cai
Journal:  Langmuir       Date:  2011-02-09       Impact factor: 3.882

6.  One-pot three-step synthesis of 1,2,3-triazoles by copper-catalyzed cycloaddition of azides with alkynes formed by a Sonogashira cross-coupling and desilylation.

Authors:  Frédéric Friscourt; Geert-Jan Boons
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

7.  Discovering the distinct inhibitory effects between C4-epimeric glycosyl amino acids: new insight into the development of protein tyrosine phosphatase inhibitors.

Authors:  Xiao-Peng He; Cui Li; Zhi-Zhou Wang; Li-Xin Gao; Xiao-Xin Shi; Yun Tang; Juan Xie; Jia Li; Guo-Rong Chen; Kaixian Chen
Journal:  Glycoconj J       Date:  2011-09-06       Impact factor: 2.916

8.  Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles.

Authors:  Adam Meares; Andrius Satraitis; Joshua Akhigbe; Nithya Santhanam; Subramani Swaminathan; Melanie Ehudin; Marcin Ptaszek
Journal:  J Org Chem       Date:  2017-06-05       Impact factor: 4.354

9.  Three-Component Protein Modification Using Mercaptobenzaldehyde Derivatives.

Authors:  Yuanwei Dai; Jiaping Weng; Justin George; Huan Chen; Qishan Lin; Jun Wang; Maksim Royzen; Qiang Zhang
Journal:  Org Lett       Date:  2019-05-06       Impact factor: 6.005

10.  Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation.

Authors:  Lindsay E Chatkewitz; John F Halonski; Marshall S Padilla; Douglas D Young
Journal:  Bioorg Med Chem Lett       Date:  2017-12-06       Impact factor: 2.823

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