4.6 Review

Isocyanide-Based Multicomponent Reactions Promoted by Visible Light Photoredox Catalysis

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

High Triplet Energy Iridium(III) Isocyanoborato Complex for Photochemical Upconversion, Photoredox and Energy Transfer Catalysis

Lucius Schmid et al.

Summary: This study reports on a new Ir(III) luminophore with an unusually high triplet energy near 3.0 eV, achieved through the modification of a previously reported Ir(III) complex with isocyanoborato ligands. The introduction of B(C6F5)(3) units in the second coordination sphere improves its photophysical properties, resulting in a high luminescence quantum yield and a long excited-state lifetime. This newly developed Ir(III) complex demonstrates enhanced photocatalytic activity in challenging organic triplet photoreactions and (sensitized) triplet-triplet annihilation upconversion, even in the ultraviolet region. The study showcases the potential of rational ligand design in transition-metal complexes for applications in solar energy conversion and synthetic photochemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Visible-light photocatalytic metal-free multicomponent Ugi-like chemistry

Camilla Russo et al.

Summary: The possibility of utilizing the photoactivity of isocyanides in metal-free multicomponent reactions has been explored in this study. The developed reactions have shown good yields and a wide scope of substrates, enabling the synthesis of diverse and complex compounds in accordance with the principles of green chemistry.

GREEN CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Photomicellar Catalyzed Synthesis of Amides from Isocyanides: Optimization, Scope, and NMR Studies of Photocatalyst/Surfactant Interactions

Alfonso Carotenuto et al.

Summary: The merging of micellar and photoredox catalysis enables efficient photochemical transformations in water. This study presents a photomicellar catalyzed synthesis of amides with a wide substrate scope and good functional group tolerance. Additionally, solution NMR experiments with paramagnetic probes provide valuable insights into the reaction environment and the localization of the photocatalyst within the micelles.

ACS ORGANIC & INORGANIC AU (2022)

Article Chemistry, Organic

The Dark Side of Isocyanides: Visible-Light Photocatalytic Activity in the Oxidative Functionalization of C(sp3)-H Bonds

Camilla Russo et al.

Summary: This study demonstrates the potential of using aromatic isocyanides as visible-light photocatalysts for a-amino C(sp(3))-H functionalization, successfully achieving a three-component crossdehydrogenative coupling reaction with high yields and a good substrate scope. The use of a catalytic loading of aromatic isocyanide also promotes the oxidative coupling of N-phenyl-1,2,3,4-tetrahydroisoquinoline with various different (pro)nucleophiles, showing promise in developing a new class of highly tunable organic visible-light photocatalysts.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Physical

Photoinduced Metal-Free α-C(sp3)-H Carbamoylation of Saturated Aza-Heterocycles via Rationally Designed Organic Photocatalyst

Ming-Jun Yi et al.

Summary: This study presents a general strategy for designing efficient organic photocatalysts and describes a method for direct C(sp(3))-H carbamoylation of saturated aza-heterocycles using a naphthalimide (NI)-based organic photocatalyst. The protocol allows for rapid installation of amide bonds onto pharmaceutically valuable saturated aza-heterocycles to access a wide range of cyclic alpha-amino amides through a visible-light photocatalytic, oxidative Ugi reaction process.

ACS CATALYSIS (2021)

Article Chemistry, Organic

Into the Blue: Ketene Multicomponent Reactions under Visible Light

Pietro Capurro et al.

Summary: A study on photophysical properties and photoreactivity of variously substituted diazoketones under blue LED irradiation revealed that all α-diazoketones can efficiently undergo Wolff rearrangement. The presence of isocyanides and carboxylic acids/silanols did not affect the photoreactivity, leading to improved selectivity and a broader scope of multicomponent reactions. These photoinduced reactions can be combined with other visible-light-mediated transformations to increase molecular diversity.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives

Camilla Russo et al.

Summary: A new visible-light photocatalytic multicomponent reaction has been developed for the synthesis of 1,3,4-oxadiazole derivatives, with good functional group tolerance and a broad substrate scope. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines has been reported. This method is particularly useful for late-stage functionalization of amino acids and drugs.

SYNTHESIS-STUTTGART (2021)

Article Chemistry, Multidisciplinary

The 100 facets of the Passerini reaction

Luca Banfi et al.

Summary: This perspective celebrates the 100th anniversary of the discovery of the Passerini three component reaction, highlighting its importance and application in organic synthesis. The focus of this review is on the various ways to expand the utility of the Passerini reaction.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Rolando Cannalire et al.

Summary: Late stage functionalization is a powerful tool for accelerating the identification of structure-activity relationships and optimizing ADME profiles of drugs. Visible-light photocatalysis offers a smooth and clean functionalization approach for drugs, with a critical assessment of current literature and highlighting expected future progress and potential applications in the field.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Applied

Mild C-F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm

Frauke Weidlich et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Multidisciplinary Sciences

Chemistry glows green with photoredox catalysis

Giacomo E. M. Crisenza et al.

NATURE COMMUNICATIONS (2020)

Review Chemistry, Applied

Photocatalytical and Photochemical Generation of Imidoyl Radicals: Synthetic Applications

Shivani Sharma et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Biochemistry & Molecular Biology

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Jurrien W. Collet et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

Visible-Light-Induced Passerini Multicomponent Polymerization

Bryan T. Tuten et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Angled Vortex Fluidic Mediated Multicomponent Photocatalytic and Transition Metal-Catalyzed Reactions

Louisa A. Ho et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Organic

Transformations of Isonitriles with Bromoalkanes Using Photoredox Gold Catalysis

Samantha Rohe et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Visible light accelerated hydrosilylation of alkynes using platinum-[acyclic diaminocarbene] photocatalysts

Jack C. Gee et al.

CHEMICAL COMMUNICATIONS (2018)

Review Chemistry, Organic

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

Mariateresa Giustiniano et al.

SYNTHESIS-STUTTGART (2018)

Article Chemistry, Organic

Dehydrogenative Transformations of Imines Using a Heterogeneous Photocatalyst

Colby M. Adolph et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Applied

A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles

Marco Malacarne et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Review Chemistry, Multidisciplinary

Chromium(0), Molybdenum(0), and Tungsten(0) Isocyanide Complexes as Luminophores and Photosensitizers with Long-Lived Excited States

Laura A. Bueldt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis

Mariateresa Giustiniano et al.

CHEMICAL SOCIETY REVIEWS (2017)

Review Biochemistry & Molecular Biology

Groebke-Blackburn-Bienaym, multicomponent reaction: emerging chemistry for drug discovery

Saad Shaaban et al.

MOLECULAR DIVERSITY (2016)

Article Chemistry, Multidisciplinary

A Molybdenum(0) Isocyanide Analogue of Ru(2,2-Bipyridine)32+: A Strong Reductant for Photoredox Catalysis

Laura A. Buldt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Iodinated (Perfluoro)alkyl Quinoxalines by Atom Transfer Radical Addition Using ortho-Diisocyanoarenes as Radical Acceptors

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Photoinduced Multicomponent Reactions

Silvia Garbarino et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Efficient photolytic C-H bond functionalization of alkylbenzene with hypervalent iodine(III) reagent

Ryu Sakamoto et al.

CHEMICAL COMMUNICATIONS (2016)

Review Chemistry, Organic

Recent progress in imidoyl radical-involved reactions

Jian Lei et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Review Chemistry, Organic

External-Oxidant-Based Multicomponent Reactions

Lisa Moni et al.

SYNTHESIS-STUTTGART (2016)

Article Chemistry, Multidisciplinary

Silver-Catalyzed Cross-Coupling of Isocyanides and Active Methylene Compounds by a Radical Process

Jianquan Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Photoredox catalysis under shear using thin film vortex microfluidics

Michael N. Gandy et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation

Abhishek Dewanji et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Article Chemistry, Organic

Toward a Green Atom Economy: Development of a Sustainable Multicomponent Reaction

Silvia Garbarino et al.

SYNTHESIS-STUTTGART (2015)

Article Chemistry, Multidisciplinary

Ketene Three-Component Reaction: A Metal-Free Multicomponent Approach to Stereodefined Captodative Olefins

Andrea Basso et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Organic

Visible Light Photoredox-Catalyzed Multicomponent Reactions

Magnus Rueping et al.

ORGANIC LETTERS (2013)

Review Chemistry, Organic

Imidoyl radicals in organic synthesis

Matteo Minozzi et al.

CURRENT ORGANIC CHEMISTRY (2007)

Article Chemistry, Organic

Highly selective double chalcogenation of isocyanides with disulfide-diselenide mixed systems

Kaname Tsuchii et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Article Chemistry, Multidisciplinary

IBX-mediated oxidative Ugi-type multicomponent reactions: Application to the N and Cl functionalization of tetrahydroisoquinoline

Tifelle Ngouansavanh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Chemistry, Multidisciplinary

Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of O-iodoxybenzoic acid

Tifelle Ngouansavanh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)