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Literature DB >> 24481643

Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds.

Hongyin Gao¹, Qing-Long Xu, Muhammed Yousufuddin, Daniel H Ess, László Kürti.

Abstract

We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations.

Entities: Chemical

Keywords: N-heterocycles; carbazoles; electrophilic amination; nitrobiaryls; regioselectivity

Mesh：

Substances：

Year: 2014 PMID： 24481643 DOI： 10.1002/anie.201309973

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

16 in total

1. PEt₃-Mediated Deoxygenative C-N Coupling of Nitroarenes and Boronic Acids.

Authors: Trevor V Nykaza; Junyu Yang; Alexander T Radosevich
Journal: Tetrahedron Date: 2019-03-25 Impact factor: 2.457

2. P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors: Gen Li; Ziyang Qin; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2020-09-11 Impact factor: 15.419

3. Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles.

Authors: Shao-Cong Zhan; Ren-Jie Fang; Jing Sun; Chao-Guo Yan
Journal: Beilstein J Org Chem Date: 2022-07-07 Impact factor: 2.544

4. I(III)-Catalyzed Oxidative Cyclization-Migration Tandem Reactions of Unactivated Anilines.

Authors: Tianning Deng; Emily Shi; Elana Thomas; Tom G Driver
Journal: Org Lett Date: 2020-10-30 Impact factor: 6.005

5. Biphilic Organophosphorus-Catalyzed Intramolecular C_sp²-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations.

Authors: Trevor V Nykaza; Antonio Ramirez; Tyler S Harrison; Michael R Luzung; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2018-02-12 Impact factor: 15.419

10. Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.

Authors: Yingwei Zhao; Haoran Zhu; Siyoung Sung; Donald J Wink; Joseph M Zadrozny; Tom G Driver
Journal: Angew Chem Int Ed Engl Date: 2021-07-20 Impact factor: 16.823

Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds.

1. PEt₃-Mediated Deoxygenative C-N Coupling of Nitroarenes and Boronic Acids.

2. P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

3. Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles.

4. I(III)-Catalyzed Oxidative Cyclization-Migration Tandem Reactions of Unactivated Anilines.

5. Biphilic Organophosphorus-Catalyzed Intramolecular C_sp²-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations.

6. Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by P^III/P^V═O Catalysis.

7. P^III /P^V =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

8. Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

9. Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes.

10. Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.