Recent advances in multi-component reactions and their mechanistic insights: a triennium review
27 Jul 2021-Organic chemistry frontiers (The Royal Society of Chemistry)-Vol. 8, Iss: 15, pp 4237-4287
TL;DR: Multi-component reactions (MCRs) are considered to be an important methodological arsenal in synthetic and medicinal chemistry as mentioned in this paper, and they have been strategically employed in various synthetic transformations where classical methods usually involve many steps with tedious procedures.
Abstract: Multi-component reactions (MCRs) are considered to be an important methodological arsenal in synthetic and medicinal chemistry. These reactions have been strategically employed in various synthetic transformations where classical methods usually involve many steps with tedious procedures. The MCR approach provides high yields, atom-/step economy, reduced reaction time, is eco-friendly, and acts as an amenable tool for the generation of a library of new chemical entities (NCEs), especially in the drug discovery process. Extensive research has led to copious developments in the field of MCRs. The developments have emerged with different synthetic approaches, including C–H activation, coupling, and cycloaddition, and eventually, such an amalgamation has enabled access to a broad spectrum of organic frameworks. The present review summarizes recent advancements in MCRs and their mechanistic insights from the last triennium (2017–2020).
Citations
More filters
TL;DR: In this article , two lacunary polyoxometalate (POM) based heterogeneous catalysts (TBA)9[BW11O39]·11H2O ((TBA,9BW11) and (Taba)6[Zr(OH)BW11 O39]−8H2 O ((Tba)6BZrW11) (Tba+: tetrabutylammonium) were synthesized and fully characterized using different techniques.
17 citations
01 Jan 2022
TL;DR: In this article , pyromellitic diamide-diacid bridged mesoporous organosilica nanospheres with controllable morphologies and acidic centers were designed and prepared through a convenient method by altering the addition sequence of precursors, solvent, and aging time.
Abstract: Novel pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies and acidic centers were designed and prepared through a convenient method by altering the addition sequence of precursors, solvent, and aging time.
11 citations
DOI•
01 Jan 2022TL;DR: In this article, pyromellitic diamide-diacid bridged mesoporous organosilica (PMAMOS) nanospheres with controllable morphologies and Bronsted acid catalytic centers were designed and prepared through a convenient method by altering the addition sequence of precursors, solvent, and aging time.
Abstract: In this work, novel pyromellitic diamide–diacid bridged mesoporous organosilica (PMAMOS) nanospheres with controllable morphologies and Bronsted acid catalytic centers were designed and prepared through a convenient method by altering the addition sequence of precursors, solvent, and aging time. The obtained PMAMOSs demonstrate high surface areas and uniform pore sizes. FESEM, HRTEM, BET, EDX, XRD, FTIR and TGA analyses were performed to characterize and examine the effective factors for the preparation of PMAMOS nanospheres. Due to the appropriate physicochemical properties including Bronsted acid centers, suitable surface area and thermal stability of the PMAMOS nanosphere material, it was explored in the three-component reaction of benzyl or benzoin, ammonium acetate, and different aldehyde derivatives as a case study of multicomponent reactions. Corresponding imidazole derivatives were obtained in EtOH under reflux conditions in high to quantitative yields and short reaction times. It was also shown that the heterogeneous solid acid can be reused at least five times with negligible loss of its catalytic activity, indicating the appropriate stability and high activity of the newly introduced mesoporous organosilica.
11 citations
TL;DR: In this article , an electrocatalytic three-component reaction was developed to construct multifunctional and valuable isothiourea compounds, which uses thiols, isocyanides and amines as substrates.
Abstract: The simultaneous binding/dissociation of multiple bonds in a one-pot manner by multicomponent reactions provide an important approach for developing novel and sustainable pathway in the drug discovery process. Herein we develop an electrocatalytic three-component reaction to construct multifunctional and valuable isothiourea compounds, which uses thiols, isocyanides and amines as substrates. Compared with the previous work, the organic electrosynthesis technique can avoid the requirement of heavy metal catalysts and stoichiometric oxidants. In addition, using thiol as a substrate to participate in the three-component reaction broadens the source of sulfur, which can also construct more abundant isothiourea derivatives.
10 citations
TL;DR: This review attempts to discuss multicomponent reactions catalysed by operationally heterogeneous catalysts in the past 10 years and a further distinction is made between the MCRs which lead to the formation of heterocycles and those which do not.
Abstract: Multicomponent reactions (MCRs) have been gaining significance and attention over the past decade because of their ability to furnish complex products by using readily available and simple starting materials while simultaneously eliminating the need to separate and purify any intermediates. More so, most of these products have been found to exhibit diverse biological activities. Another paradigm shift which has occurred contemporarily is the switch to heterogeneous catalysis, which results in additional benefits such as the reduction of waste and an increase in the safety of the process. More importantly, it allows the user to recover and reuse the catalyst for multiple runs. In summary, both methodologies adhere to the principles of green chemistry, a philosophy which needs to become overarchingly enshrined. The plethora of reactions and catalysts which have been developed gives hope that chemists are slowly changing their ideology. As a result, this review attempts to discuss multicomponent reactions catalysed by operationally heterogeneous catalysts in the past 10 years. In this review, a further distinction is made between the MCRs which lead to the formation of heterocycles and those which do not.
9 citations
References
More filters
TL;DR: This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
Abstract: The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
2,391 citations
TL;DR: Several facets of these kinds of C–H functionalization reactions are discussed and a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents are provided.
Abstract: Novel reactions that can selectively functionalize carbon-hydrogen bonds are of intense interest to the chemical community because they offer new strategic approaches for synthesis. A very promising 'carbon-hydrogen functionalization' method involves the insertion of metal carbenes and nitrenes into C-H bonds. This area has experienced considerable growth in the past decade, particularly in the area of enantioselective intermolecular reactions. Here we discuss several facets of these kinds of C-H functionalization reactions and provide a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents.
1,843 citations
TL;DR: This paper presents a new approach to drug design called “combinatorial biosynthesis and drug discovery through nanofiltration”, which combines the efforts of a single investigator with those of a number of other scientists.
Abstract: Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, … 7, where most of the atoms of the starting materials are incorporated in the final product.1 Several descriptive tags are regularly attached to MCRs (Fig. 1): they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in one-step instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2 Therefore MCRs are often a useful alternative to sequential multistep synthesis.
Open in a separate window
Figure 1
Above: multistep syntheses can be divergent (sequential) or convergent; below: in analogy MCR reactions are convergent and one or two component reactions are divergent or less convergent.
1,840 citations
TL;DR: The ability to design COFs and to adjust their pore metrics using the principles of reticular synthesis has given rise to frameworks with ultralow densities, which has resulted in the first implementation of the concept of molecular weaving.
Abstract: Just over a century ago, Lewis published his seminal work on what became known as the covalent bond, which has since occupied a central role in the theory of making organic molecules. With the advent of covalent organic frameworks (COFs), the chemistry of the covalent bond was extended to two- and three-dimensional frameworks. Here, organic molecules are linked by covalent bonds to yield crystalline, porous COFs from light elements (boron, carbon, nitrogen, oxygen, and silicon) that are characterized by high architectural and chemical robustness. This discovery paved the way for carrying out chemistry on frameworks without losing their porosity or crystallinity, and in turn achieving designed properties in materials. The recent union of the covalent and the mechanical bond in the COF provides the opportunity for making woven structures that incorporate flexibility and dynamics into frameworks.
1,687 citations
1,273 citations