Towards click chemistry: Multicomponent reactions via combinations of name reactions

Heravi, Majid Μ.; Zadsirjan, Vahideh; Dehghani, Mahzad; Ahmadi, Tahereh

doi:10.1016/j.tet.2018.04.076

Cited by 56 publications

(17 citation statements)

References 229 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[15][16][17] In this work, the described combination of a plug-flow catalytic microreactor and an automated flow system allows us to resolve in a fast and convenient manner the kinetics of a primary-amine catalyzed KnoevenagelÀ Michael domino reaction to tetrahydrochromene derivatives (Scheme 1). The importance of multicomponent domino reactions, in general, as well as of the chosen reaction system, in particular, have been broadly covered over the years and in recent reports, [18][19][20][21][22][23] so that we will not discuss further details here. However, even with a wide variety of catalysts and a large number of proposed reaction mechanisms reported, a systematic investigation on how a catalyst is capable of catalyzing simultaneously two different reactions is missing.…”

Section: Introductionmentioning

confidence: 99%

Kinetics Studies on a Multicomponent Knoevenagel−Michael Domino Reaction by an Automated Flow Reactor

Haas

Tallarek

2019

ChemistryOpen

View full text Add to dashboard Cite

The optimization of complex chemical reaction systems is often a troublesome and time‐consuming process. The application of modern technologies, including automated reactors and analytics, opens the avenue for generating large data sets on chemical reaction processes in a short period of time. In this work, an automated flow reactor is used to present detailed kinetics and mechanistic studies about an amine‐catalyzed Knoevenagel−Michael domino reaction to yield tetrahydrochromene derivatives. High‐performance monoliths as catalyst supports and online coupled HPLC analysis allow for time‐efficient data generation. We show that the two‐step multicomponent domino reaction does not follow the kinetics of consecutive reaction steps proceeding independently from each other. Instead, the starting materials of both individual reactions compete for the active sites on the heterogeneous catalyst, which lowers the rate constants of both steps. This knowledge was used to implement a more efficient experimental setup which increased the turnover numbers of the catalyst, without adjusting common reaction parameters like temperature, reaction time, and concentrations.

show abstract

Section: Introductionmentioning

confidence: 99%

Kinetics Studies on a Multicomponent Knoevenagel−Michael Domino Reaction by an Automated Flow Reactor

Haas

Tallarek

2019

ChemistryOpen

View full text Add to dashboard Cite

show abstract

“…Several multi-component reactions have been designed in an ecofriendly manner like aldol condensation followed by Michael addition, Ugi reaction/aldol reaction, Ugi reaction/Huisgen reaction, Ugi Reaction/Diels-Alder reaction, Ugi reaction/Heck reactions, Michael addition/Mannich reaction, etc. [23] The most famous click reaction is the classical reaction between an azide and an alkyne. Both the substrates do not react under physiological conditions and go through a cycloaddition reaction only at a particular temperature.…”

Section: Classification Of Click Reactionmentioning

confidence: 99%

Role of Click Chemistry in Organic Synthesis

Sethiya¹,

Sahiba²,

Agarwal³

2021

Current Topics in Chirality - From Chemistry to Biology

View full text Add to dashboard Cite

Click chemistry involves highly efficient organic reactions of two or more highly functionalized chemical entities under eco-benign conditions for the synthesis of different heterocycles. Several organic reactions such as nucleophilic ring-opening reactions, cyclo-additions, nucleophilic addition reactions, thiol-ene reactions, Diels Alder reactions, etc. are included in click reactions. These reactions have very important features i.e. high functional group tolerance, formation of a single product, high atom economy, high yielding, no need for column purification, etc. It also possesses several applications in drug discovery, supramolecular chemistry, material science, nanotechnology, etc. Being highly significant and valuable, we have elaborated on several aspects of click reactions in organic synthesis in this chapter. Recent advancements in the field of organic synthesis using click chemistry approach have been deliberated by citing last five years articles.

show abstract

“…Organic chemists have devoted considerable effort to the development of reactions in which a series of chemical transformations occur (with multiple bonds being formed and/or broken) without the requirement of isolating intermediates or signicantly changing reaction conditions. [1][2][3][4][5][6] Despite efforts to dene and classify these types of reactions, they are oen indiscriminately termed cascade, tandem, or domino reactions. 1,[7][8][9] Cascade reactions are oen pursued for their increased synthetic efficiency, as they help enable the synthesis of complex molecules with decreased number of reaction and workup steps, as well as potentially reducing the quantities of chemical reagents, solvents, byproducts, and waste.…”

Section: Introductionmentioning

confidence: 99%

Cascade polymerizations: recent developments in the formation of polymer repeat units by cascade reactions

Peterson

Choi

2020

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Towards click chemistry: Multicomponent reactions via combinations of name reactions

Cited by 56 publications

References 229 publications

Kinetics Studies on a Multicomponent Knoevenagel−Michael Domino Reaction by an Automated Flow Reactor

Kinetics Studies on a Multicomponent Knoevenagel−Michael Domino Reaction by an Automated Flow Reactor

Role of Click Chemistry in Organic Synthesis

Cascade polymerizations: recent developments in the formation of polymer repeat units by cascade reactions

Contact Info

Product

Resources

About