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Literature DB >> 24274154

6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).

Dirk Leifert¹, Constantin Gabriel Daniliuc, Armido Studer.

Abstract

Readily accessible 2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imidoyl radicals. Initiation of the radical chain reaction is best achieved with small amounts of FeCl3 (0.4 mol %), and the commercially available and cheap tBuOOH is used as the oxidant.

Entities: Chemical

Mesh：

Substances：
Aldehydes
Phenanthridines

Year: 2013 PMID： 24274154 DOI： 10.1021/ol403147v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

Review 1. The electron is a catalyst.

Authors: Armido Studer; Dennis P Curran
Journal: Nat Chem Date: 2014-09 Impact factor: 24.427

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

Review 3. Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

Authors: Lidija-Marija Tumir; Marijana Radić Stojković; Ivo Piantanida
Journal: Beilstein J Org Chem Date: 2014-12-10 Impact factor: 2.883

4. Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

Authors: Chao Che; Qianwen Huang; Hanliang Zheng; Gangguo Zhu
Journal: Chem Sci Date: 2016-03-04 Impact factor: 9.825

9. Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

Authors: Mong-Feng Chiou; Haigen Xiong; Yajun Li; Hongli Bao; Xinhao Zhang
Journal: Molecules Date: 2020-03-09 Impact factor: 4.411

9 in total

6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).

Review 1. The electron is a catalyst.

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Review 3. Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

4. Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

5. Photocatalytic reverse polarity Povarov reaction.

6. Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs.

7. PPh₃/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls.

8. Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.

9. Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).

Review 1. The electron is a catalyst.

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Review 3. Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

4. Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

5. Photocatalytic reverse polarity Povarov reaction.

6. Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs.

7. PPh3/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls.

8. Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.

9. Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

7. PPh₃/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls.