Isocyanide‐Based Multicomponent Reactions Promoted by Visible Light Photoredox Catalysis

Russo, Camilla; Brunelli, Francesca; Tron, Gian Cesare; Giustiniano, Mariateresa

doi:10.1002/chem.202203150

Cited by 24 publications

(14 citation statements)

References 86 publications

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“…Thus, isocyanides hold promise for interesting new applications beyond synthesis in different areas, including medicine and materials. The medicinal chemistry of isocyanides has recently been comprehensively reviewed. − …”

Section: Introductionmentioning

confidence: 99%

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Chatziorfanou,

Romero,

Chouchane

et al. 2024

J. Org. Chem.

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The isocyanide group is the chameleon among the functional groups in organic chemistry. Unlike other multiatom functional groups, where the electrophilic and nucleophilic moieties are typically separated, isocyanides combine both functionalities in the terminal carbon. This unique feature can be rationalized using the frontier orbital concept and has significant implications for its intermolecular interactions and the reactivity of the functional group. In this study, we perform a Cambridge Crystallographic Database-supported analysis of isocyanide intramolecular interactions to investigate the intramolecular interactions of isocyanides in the solid state, excluding isocyanide−metal complexes. We discuss examples of different interaction classes, including the isocyanide as a hydrogen bond acceptor (RNC•••HX), halogen bonding (RNC•••X), and interactions involving the isocyanide and carbon atoms (RNC•••C). The latter interaction serves as an intriguing illustration of a Burgi−Dunitz trajectory and represents a crucial experimental detail in the well-known multicomponent reactions such as the Ugi-and Passerini-type mechanisms. Understanding the spectrum of intramolecular interactions that isocyanides can undergo holds significant implications in fields such as medicinal chemistry, materials science, and asymmetric catalysis.

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Section: Introductionmentioning

confidence: 99%

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Chatziorfanou,

Romero,

Chouchane

et al. 2024

J. Org. Chem.

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“…Classical multicomponent reactions are well known by their proper name and scope: Ugi [ 4 , 9 ], Passerini [ 6 , 10 ], van Leusen [ 11 , 12 ], Strecker [ 13 ], Orru [ 14 ], Mannich [ 6 , 15 ], Biginelli [ 6 , 16 , 17 ] and Hantzsch syntheses [ 6 , 18 ] need to be mentioned. However, the discovery of new multicomponent reactions is an active research field [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], with novel exciting MCRs being discovered and incorporated to the synthetic armamentarium every year. Among these MCRs with transition metal catalysis [ 28 , 29 , 30 , 31 , 32 , 33 , 34 ], radical process [ 7 , 21 , 35 , 36 ] and organo-catalysis [ 37 , 38 , 39 , 40 , 41 ] should also be mentioned.…”

Section: Introduction: Multicomponent Reactionsmentioning

confidence: 99%

Multicomponent Reaction-Assisted Drug Discovery: A Time- and Cost-Effective Green Approach Speeding Up Identification and Optimization of Anticancer Drugs

Graziano

Stefanachi

Contino

et al. 2023

IJMS

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Multicomponent reactions (MCRs) have emerged as a powerful strategy in synthetic organic chemistry due to their widespread applications in drug discovery and development. MCRs are flexible transformations in which three or more substrates react to form structurally complex products with high atomic efficiency. They are being increasingly appreciated as a highly exploratory and evolutionary tool by the medicinal chemistry community, opening the door to more sustainable, cost-effective and rapid synthesis of biologically active molecules. In recent years, MCR-based synthetic strategies have found extensive application in the field of drug discovery, and several anticancer drugs have been synthesized through MCRs. In this review, we present an overview of representative and recent literature examples documenting different approaches and applications of MCRs in the development of new anticancer drugs.

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“…The combination of photoredox-catalyzed radical chemistry with multicomponent reactions (MCRs) enables the rapid and atom-efficient construction of complex scaffolds in one-pot fashion. 1,2 The atom-transfer radical addition (ATRA), in particular, offers elegant solutions for the chemo-and regioselective 1,2-difunctionalizations of olefins. 3,4 The common mechanistic feature of these radical-polar crossover reactions includes (i) photocatalytic radical generation, (ii) the addition of the radical formed to an alkene, (iii) oxidation of the resulting radical intermediate via single electron transfer (SET), and (iv) trapping of the formed carbocation by a nucleophile (Figure 1a).…”

Section: ■ Introductionmentioning

confidence: 99%

Visible-Light-Induced Synthesis of Branched Ethers via Multicomponent Reactions

Győrfi

Tasnádi²,

Gyuris³

et al. 2023

J. Org. Chem.

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The Spin-Center Shift (SCS) elimination is a specific way for the generation of radicals with relevance in synthetic and biochemical pathways. The combination of SCS-mediated radical chemistry and atom-transfer radical addition (ATRA) offers new directions in diversity-oriented chemical synthesis. Herein, we report a photoredox three-component reaction of α-acyloxy-N-heterocycles as radical precursors, styrene derivatives as radical trapping agents, and alcohols as nucleophilic quenchers. The novel radical-polar crossover reaction provides access to a diverse set of branched ethers possessing high structural complexity. The utility of the transformation was also demonstrated by the synthesis of a complex drug derivative and it was easily scalable to the multigram level. The scope and limitations were also explored and a plausible mechanism was proposed.

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Isocyanide‐Based Multicomponent Reactions Promoted by Visible Light Photoredox Catalysis

Abstract: Scheme 3. Titanium dioxide promoted Ugi-like 3CR involving tertiary aromatic amines, isocyanides and water. Scheme 4. Metal-free photoredox catalyzed Ugi-like 3CR under continuous flow conditions. Scheme 5. Metal-free photoredox catalyzed Ugi-like 3CR using thin film vortex microfluidics.

Cited by 24 publications

References 86 publications

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Multicomponent Reaction-Assisted Drug Discovery: A Time- and Cost-Effective Green Approach Speeding Up Identification and Optimization of Anticancer Drugs

Visible-Light-Induced Synthesis of Branched Ethers via Multicomponent Reactions

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