4.5 Review

Recent Advancements in Synthesis of Phenanthridines via 2-Isocyanobiphenyls

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Article Chemistry, Organic

Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines

Jin-Yang Chen et al.

Summary: A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene(4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodoniumylides was established for the synthesis of 6-arylated phenanthridines. This is the first example of employing iodonium ylides as aryl radical sources in a visible-light-induced radical cascade cyclization reaction.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

Yan Liu et al.

Summary: 4,5,6-Tetrakis (3,6-di-tert-butyl-9H-carbazol-9-yl)-isophthalonitrile (4CzIPN-Bu-t) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-Bu-t as catalyst, a visible light-induced proton-coupled electron transfer strategy was developed for the generation of phosphorus-centered radicals, leading to the successful construction of phosphorylated phenanthridines, quinolines, and benzothiazoles.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

Songeziwe Ntsimango et al.

Summary: UV radiation was used to transform readily synthesized biphenyl-2-carbaldehyde O-acetyl oximes into phenanthridines, with the scope and limitations of this novel reaction explored. The methodology was successfully applied in the synthesis of trisphaeridine, achieving a 6.5% overall yield from 1-bromo-2,4,5-trimethoxybenzene in four linear steps.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Synthesis of hexahydrophenanthridines via the tandem reaction of benzynes

Wen-Juan Li et al.

TETRAHEDRON (2020)

Article Chemistry, Applied

Four Pathways in Radical Alkylation of Isocyanide with Simple Alcohol

Shuai Liu et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Chemistry, Organic

Transformations of Isonitriles with Bromoalkanes Using Photoredox Gold Catalysis

Samantha Rohe et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Cascade double isocyanide insertion and C-N coupling of 2-iodo-2-isocyano-1,1-biphenyls

Hongwei Sun et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Article Chemistry, Organic

Dissymmetric Bay-Functionalized Perylenediimides

Kapil Kumar et al.

SYNLETT (2018)

Article Chemistry, Organic

Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives

Xiangyu Liu et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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)

Article Chemistry, Multidisciplinary

Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis

Jian Rong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Silver-catalyzed oxidative decarboxylation of difluoroacetates: efficient access to C-CF2 bond formation

Wen Wan et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Organic

Metal-Free Synthesis of 6-Phosphorylated Phenanthridines: Synthetic and Mechanistic Insights

Ludovik Noel-Duchesneau et al.

ORGANIC LETTERS (2016)

Article Chemistry, Organic

Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction

Aaron L. Brown et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Organic

Ni-catalyzed reductive addition of alkyl halides to isocyanides

Bo Wang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

Article Spectroscopy

Study of interaction between human serum albumin and three phenanthridine derivatives: Fluorescence spectroscopy and computational approach

Jianming Liu et al.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2015)

Article Chemistry, Applied

Di-tert Butyl Peroxide-Promoted Sequential Methylation and Intramolecular Aromatization of Isonitriles

Qiang Dai et al.

ADVANCED SYNTHESIS & CATALYSIS (2014)

Article Chemistry, Multidisciplinary

The benzoyl peroxide-promoted functionalization of simple alkanes with 2-aryl phenyl isonitrile

Wanxing Sha et al.

CHEMICAL COMMUNICATIONS (2014)

Article Chemistry, Organic

A Free Radical Cascade Cyclization of Isocyanides with Simple Alkanes and Alcohols

Zejiang Li et al.

ORGANIC LETTERS (2014)

Article Chemistry, Organic

An efficient synthesis of (NH)-phenanthridinones via ligand-free copper-catalyzed annulation

Yan-Fu Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2014)

Article Chemistry, Organic

Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives

Yuanzheng Cheng et al.

ORGANIC LETTERS (2013)

Article Chemistry, Organic

6-Aroylated Phenanthridines via Base Promoted Homolytic Aromatic Substitution (BHAS)

Dirk Leifert et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

Roy T. McBurney et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Organic

Synthesis of Phenanthridine Derivatives via Photolysis

Anna M. Linsenmeier et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Two color RNA intercalating probe for cell imaging applications

Nathan Stevens et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Organic

New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines

Rafael Alonso et al.

ORGANIC LETTERS (2006)

Article Chemistry, Multidisciplinary

Total synthesis of ecteinascidin 743

A Endo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Medicinal

One-pot synthesis and biological evaluation of aspergillamides and analogues

B Beck et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2000)