4.7 Article

Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C-C Bond Cleavage/Cyclization of N-Functionalized Acrylamides

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Iron-Catalyzed Alkoxyl Radical-Induced C-C Bond Cleavage/gem-Difluoroalkylation Cascade

Tian-Yu Zhang et al.

Summary: An inexpensive iron-catalyzed alkoxylradical-induced C-C bond cleavage/gem-difluoroalkylation cascade is developed. Fluorinated distal diketones are synthesized via a ring-opening strategy regulated by the structure of alkoxyl radical precursors, while difluoroalkylated medium-sized lactones and macrolactones are constructed through a ring-expansion strategy. Both protocols show mild and redox neutral conditions, broad substrate scope, and good functional group compatibility.

ORGANIC LETTERS (2023)

Review Chemistry, Multidisciplinary

Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis

Liang Chang et al.

Summary: This review comprehensively summarizes the recent progress in alkoxy radical-mediated transformations under visible light irradiation. The mechanisms of alkoxy radical generation and their impact on synthetic utilizations are discussed. The catalytic generation of alkoxy radicals from abundant alcohols is still in the early stage, but holds great potential.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

A new approach for the copper-catalyzed functionalization of alkyl hydroperoxides with organosilicon compounds via in-situ-generated alkylsilyl peroxides

Wenfeng Zhong et al.

Summary: In this study, alkylsilyl peroxides were generated in situ from organosilicon compounds and an amine base. The alkylsilyl peroxides were then cleaved by copper catalysis to produce alkyl radicals, which reacted with nucleophiles to form coupling products with new carbon-carbon, carbon-nitrogen, or carbon-halogen bonds.

TETRAHEDRON (2022)

Article Chemistry, Organic

Free Radical Cascade Carbochloromethylations of Activated Alkenes

Zhi-Wei Zhao et al.

Summary: Free radical carbochloromethylation reactions of ortho-cyanoarylacrylamides and N-(arylsulfonyl)acrylamides have been developed using simple alkyl chlorides as the chloromethyl source. These transformations exhibit wide functional group compatibility and provide efficient methods for constructing polychloromethyl-substituted quinoline-2,4-diones and alpha-aryl-beta-polychloromethylated amides.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Photocatalytic radical cascade cyclization of N-(o-cyanobiaryl) acrylamides: access to CF2H-functionalized pyrido[4,3,2-gh] phenanthridines

Mei Zhu et al.

Summary: In this study, a simple and efficient method for the preparation of CF2H-substituted pyrido[4,3,2-gh]phenanthridines under photoredox conditions was reported. The reactions involve a cascade radical difluoromethylation/cyano insertion/cyclization, leading to the construction of three different types of bonds. This difluoromethylated transformation shows good functional group compatibility.

CHEMISTRYSELECT (2022)

Article Chemistry, Organic

Asymmetric Ketoalkylation/Rearrangement of Alkyenlfurans via Synergistic Photoredox/Br?nsted Acid Catalysis

Jie Wei et al.

Summary: An enantioselective three-component rearrangement of alkenylfurans has been developed by merging photoredox catalysis with chiral Brønsted acid catalysis. This protocol provides expedient access to a broad spectrum of ketoalkyl-functionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities. Diverse functional groups can be introduced via facile product derivations.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Photoredox aerobic oxidative cycliation of N-arylacrylamides with benzylalcohols

Ablimit Abdukader et al.

Summary: A visible-light-induced aerobic oxidative coupling/cyclization reaction has been developed for the synthesis of oxygen-containing oxindoles.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Visible-light-induced acylation/cyclization of active alkenes: facile access to acylated isoquinolinones

Yang Guo et al.

Summary: In this study, an efficient and practical visible-light-induced acylation/cyclization reaction was developed for constructing acylated indolo/benzimidazo-[2,1,a]isoquinolin-6(5H) compounds, using acyl oxime derivatives and active alkenes as substrates.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO2 insertion and radical cascade cyclization

Jie Zhang et al.

Summary: An efficient method for arylsulfonylation/cyclization of 2-aryl-N-methacryloyl indoles using potassium metabisulfite and aryldiazonium tetrafluoroborates was developed. This three-component protocol utilizes potassium metabisulfite as a SO2 surrogate, leading to the formation of variously substituted arylsulfonyl indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields. Furthermore, the method can also be utilized for the synthesis of arylsulfonyl-substituted benzimidazo-[2,1-a]isoquinolin-6(5H)-one compounds.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Copper-catalyzed amino radical tandem cyclization toward the synthesis of indolo-[2,1-a]isoquinolines

Mei-Ling Liu et al.

Summary: A convenient process for synthesizing indolo-[2,1-a]isoquinoline tetracyclic skeletons in one pot via a low-cost copper-catalyzed tandem amino radical cyclization, in which one C-C bond and one C-N bond are synchronously established, has been reported. A range of valuable indolo-[2,1-a]isoquinoline derivatives bearing various groups was obtained under mild conditions.

ORGANIC CHEMISTRY FRONTIERS (2022)

Review Chemistry, Multidisciplinary

Visible Light-Driven Radical-Mediated C-C Bond Cleavage/Functionalization in Organic Synthesis

Xiao-Ye Yu et al.

Summary: In recent years, visible light photoredox-catalyzed radical-mediated C-C bond cleavage reactions have emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C-C bond cleavage in diverse molecular scaffolds. These reactions provide an efficient way to construct structurally diverse molecular skeletons, contributing to the development in the field of synthetic organic chemistry.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones by Cerium and Cyanoanthracene Catalysis

Jianbo Du et al.

Summary: A cerium-catalyzed aerobic oxidative ring expansion method using cyanoanthracene as a co-catalyst has been developed for the rapid construction of challenging macrolactones under visible light conditions, demonstrating the potential to simplify the generation of molecular complexity and enabling the concise synthesis of sonnerlactone.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Iron-Catalyzed Ring Opening of Cyclopropanols and Their 1,6-Conjugate Addition to p-Quinone Methides

Baliram B. Mane et al.

Summary: The novel iron-catalyzed ring opening of cyclopropanols and their 1,6-conjugate addition to p-quinone methides allows for the efficient synthesis of substituted phenols. This method features simple operation, mild reaction conditions, high yields, and a wide range of substrate applicability.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Persulfate promoted tandem radical cyclization of ortho-cyanoarylacrylamides with oxamic acids for construction of carbamoyl quinoline-2,4-diones under metal-free conditions

Qing-Qing Han et al.

Summary: An efficient and practical method for synthesizing carbamoyl quinoline-2,4-diones was described using a cyclic reaction with ortho-cyanoarylacrylamides and oxamic acids under metal free conditions. Various products with functional groups could be obtained with moderate to high yields via radical mechanism.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Applied

Molecular Oxygen-Mediated Radical Cyclization of Acrylamides with Boronic Acids

Changduo Pan et al.

Summary: A new method under metal-free conditions was proposed for the synthesis of indolo[2,1-a] isoquinolinone derivatives and benzimidazo-[2,1-a]isoquinolinone derivatives via autoxidation reaction, utilizing primary and secondary alkyl boronic acids as alkyl sources with O-2 as the oxidant.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Organic

Silver-catalyzed decarboxylative radical relay difluoroalkylation-carbocyclization: convenient access to CF2-containing quinolinones

Feng Zhao et al.

Summary: A practical Ag-catalyzed decarboxylative difluoroalkylation-carbocyclization reaction was reported, yielding various gem-fluorinated quinolinones in moderate to good yields. Mechanistic studies suggested a pathway involving formal decarboxylation and subsequent radical difluoroalkylation-carbocyclization.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Visible light induced radical cascade cyclization of ortho-cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1H,3H)-dione

Yuan-Yuan Sun et al.

Summary: In this study, a visible light induced cascade cyclization reaction was used to efficiently prepare phosphorylated quinoline-2,4(1H,3H)-dione. The products were isolated with moderate to good yields, and a radical mechanism was proposed for this transformation.

NEW JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Organic

Copper-catalyzed redox neutral ketoalkylation of Csp2-H bonds via C-C bond cleavage

He Chen et al.

Summary: An efficient copper-catalyzed ketoalkylation of Csp(2)-H bonds with cycloalkyl silyl peroxides under mild and redox neutral conditions has been developed, successfully incorporating distal ketoalkyl moieties into specific positions through C-C bond cleavage with moderate to good yields.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Organic

Synthesis of Oxygen- or Nitrogen-Containing Heterocyclic Compounds via Radical Addition Cascade Cyclization

Jie Zhang et al.

Summary: Radical addition cascade cyclization is a convenient and efficient strategy for constructing various oxygen- or nitrogen-containing heterocycles, and has drawn much attention in recent years. This article provides an overview of this strategy based on the types of oxygen- or nitrogen-containing heterocyclic compounds.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer

Kuo Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Radical-Promoted C-C Bond Cleavage: A Deconstructive Approach for Selective Functionalization

Sara P. Morcillo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Recent Advances in Ring-Opening Functionalization of Cycloalkanols by C-C sigma-Bond Cleavage

Xinxin Wu et al.

CHEMICAL RECORD (2018)

Article Chemistry, Multidisciplinary

Tandem Radical Cyclization for the Construction of Difluoro-Containing Oxindoles and Quinoline-2,4-diones

Fangwei Ding et al.

CHEMISTRY-AN ASIAN JOURNAL (2018)

Article Chemistry, Multidisciplinary

Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes through Dual Photoexcitation

Anhua Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Biochemistry & Molecular Biology

Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols

Nafees Ahmed et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2010)

Article Chemistry, Medicinal

A direct synthesis of 5,6-dihydroindolo[2,1-a]isoquinolines that exhibit immunosuppressive activity

George A. Kraus et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2009)