4.6 Review

Recent progress in metal assisted multicomponent reactions in organic synthesis

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Article Chemistry, Organic

Copper-Catalyzed Regio- and Stereoselective Three-Component Coupling of Allenyl Ethers with gem-Dichlorocyclobutenones and B2pin2

Shuai Liu et al.

Summary: A three-component coupling method was reported for the regio- and stereoselective difunctionalization of allenes with allenyl ethers, bis(pinacolato)diboron, and gem-dichlorocyclobutenones as electrophiles, leading to highly functionalized cyclobutenone products tethering with an alkenylborate fragment. The polysubstituted cyclobutenone products also showed diverse transformation abilities.

ORGANIC LETTERS (2023)

Article Chemistry, Inorganic & Nuclear

Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction

Sobhan Rezayati et al.

Summary: An efficient and heterogeneous magnetic nanocatalyst Fe3O4@SiO2@GP/Picolylamine-Cu(II) was synthesized and successfully applied in Biginelli condensation for the preparation of biologically active compounds with high conversions and reusability. The catalyst system exhibited several significant advantages, including convenient and clean reaction conditions, gram-scale synthesis, usage of nontoxic solvent, improved yield, short reaction times, and high durability. Additionally, the nanocatalyst could be recycled by an external magnet for multiple runs with only a slight decrease in product yields.

INORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Fe-Catalyzed Dicarbofunctionalization of Vinylarenes with Alkylsilyl Peroxides and β-Keto Carbonyl Substrates

Weiping Xu et al.

Summary: It has been discovered that under mild reaction conditions, two carbon-carbon bonds can be formed using vinylarenes, alkylsilyl peroxides, and beta-keto carbonyl substrates with the presence of catalytic Fe(OTf)2.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Interception of Nickel Hydride Species and Its Application in Multicomponent Reactions

Venkadesh Balakrishnan et al.

Summary: The hydrogen borrowing strategy is a cost-effective method for the synthesis of alpha-functionalized ketones. However, it cannot be used for the synthesis of beta, beta-disubstituted ketones. This limitation can be overcome by intercepting the in situ generated metal hydride with a nucleophilic coupling partner. In this study, we present a multicomponent strategy for coupling alcohols, ketones, and boronic acids using only 1 mol% nickel catalyst without the need for added ligands.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

An efficient approach for 3-haloquinoline synthesis: PhI(OAc)2-mediated A3-X type tandem annulation of amine, aldehyde, alkyne and halide salt

Hongbin Lu et al.

Summary: A novel A3-X type reaction for functionalized 3-haloquinolines has been developed by utilizing simple aromatic amine, aldehyde, alkyne and halide salt through the PhI (OAc)2-mediated four-component tandem addition/cyclization/oxidation/aromatization process. The reaction exhibits broad functional group tolerance, mild conditions, and easy conversion, demonstrating its conciseness, high efficiency, and practicability.

TETRAHEDRON LETTERS (2022)

Article Chemistry, Organic

Visible-light enabled one-pot three-component Petasis reaction for synthesis of a-substituted secondary sulfonamides/amides/hydrazides

Devaiah Vytla et al.

Summary: An efficient three-component photoredox-catalyzed Petasis reaction was reported. Under optimized conditions using [Ir{dFCF(3)PPy}(2)(dtbpy)]PF6 as the photocatalyst, a wide range of sulfonamides, amides, and hydrazides efficiently underwent imine formation with various benzaldehydes followed by radical alpha-alkylation with alkyltrifluoroborates in the presence of sodium hydrogen sulfate. This operationally simple protocol allows rapid access to structurally diverse alpha-substituted secondary sulfonamides, amides, and hydrazides in moderate to high yields.

TETRAHEDRON LETTERS (2022)

Article Chemistry, Organic

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

Shuling Yu et al.

Summary: An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates was reported. The treatment of a variety of alkyl halides with a Na2CO3/MeOH solution could smoothly achieve 5-alkylation of the cyclopentenones. Excess formaldehyde and malonate led to a multicomponent reaction that afforded multisubstituted cyclopentenones through a Michael addition.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Alkylation of in situ generated imines via photoactivation of strong aliphatic C-H bonds

Serena Pillitteri et al.

Summary: The study focuses on the development of a broadly applicable strategy for the alkylation of in situ formed imines for the construction of functionalized secondary amines under mild reaction conditions. This atom economic transformation exploits the intrinsic electrophilicity of imines towards radical addition, and the fine-tuning of electronic properties of the starting materials allows the formation of a wide variety of products.

MOLECULAR CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Visible-light-mediated multicomponent reaction for secondary amine synthesis

Xiaochen Wang et al.

Summary: The study presents a simplified method for the synthesis of secondary amines through three-component alkylation reactions of imines generated by condensation of benzaldehydes and anilines with unactivated alkyl iodides. This method is operationally simple, mild, compatible with various sensitive functional groups, and does not require a large excess of the alkylating reagent.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Organic

Selectivity in multiple multicomponent reactions: types and synthetic applications

Ouldouz Ghashghaei et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2019)

Review Chemistry, Organic

Multicomponent Reactions for the Synthesis of Bioactive Compounds: A Review

Cedric S. Graebin et al.

CURRENT ORGANIC SYNTHESIS (2019)

Review Chemistry, Multidisciplinary

Multicomponent Reactions Accelerated by Aqueous Micelles

Daniel Paprocki et al.

FRONTIERS IN CHEMISTRY (2018)

Article Chemistry, Organic

Utilization of MeOH as a C1 Building Block in Tandem Three Component Coupling Reaction

Kaushik Chakrabarti et al.

ORGANIC LETTERS (2017)

Article Chemistry, Physical

Palladium-Catalyzed Enantioselective C(sp2)-H lmidoylation by Desymmetrization

Jian Wang et al.

ACS CATALYSIS (2017)

Review Chemistry, Organic

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Mohammad Haji

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

Microwave-Assisted Copper-Catalyzed Four-Component Tandem Synthesis of 3-N-Sulfonylamidine Coumarins

Govindarasu Murugavel et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Organic

Calcium-Catalyzed Dynamic Multicomponent Reaction

Shuang Gao et al.

ORGANIC LETTERS (2015)

Review Chemistry, Multidisciplinary

Recent advances in multicomponent reactions involving carbohydrates

Md Musawwer Khan et al.

RSC ADVANCES (2015)

Review Chemistry, Multidisciplinary

Small Heterocycles in Multicomponent Reactions

Benjamin H. Rotstein et al.

CHEMICAL REVIEWS (2014)

Article Chemistry, Multidisciplinary

Multicomponent reactions: advanced tools for sustainable organic synthesis

Razvan C. Cioc et al.

GREEN CHEMISTRY (2014)

Article Chemistry, Organic

Syntheses of Fused Tetracyclic Quinolines via Ugi-Variant MCR and Pd-Catalyzed Bis-annulation

Chao Che et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Physical

Palladium-Catalyzed Dehydrogenative β-Arylation of Simple Saturated Carbonyls by Aryl Halides

Parthasarathy Gandeepan et al.

ACS CATALYSIS (2014)

Review Chemistry, Multidisciplinary

Chemistry and Biology Of Multicomponent Reactions

Alexander Domling et al.

CHEMICAL REVIEWS (2012)

Review Biochemistry & Molecular Biology

Recent advances in multicomponent reactions for diversity-oriented synthesis

James E. Biggs-Houck et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2010)

Review Chemistry, Organic

Piperazine Scaffolds via Isocyanide-Based Multicomponent Reactions

Exander Doemling et al.

SYNTHESIS-STUTTGART (2010)

Review Chemistry, Multidisciplinary

Strategies for Innovation in Multicomponent Reaction Design

Bruce Ganem

ACCOUNTS OF CHEMICAL RESEARCH (2009)

Article Chemistry, Multidisciplinary

Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds

James D. Sunderhaus et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

Review Chemistry, Multidisciplinary

Multi-component syntheses of heterocycles by transition-metal catalysis

Daniel M. D'Souza et al.

CHEMICAL SOCIETY REVIEWS (2007)