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Literature DB >> 25415390

Cu(I)-catalyzed transannulation of N-heteroaryl aldehydes or ketones with alkylamines via C(sp3)-H amination.

Mingyang Li¹, Ying Xie¹, Yong Ye¹, Yong Zou², Huanfeng Jiang¹, Wei Zeng¹.

Abstract

A copper(I)-catalyzed direct transannulation of N-heteroaryl aldehydes or ketones with alkylamines via Csp(3)-H amination has been achieved using molecular oxygen as a sole oxidant. N-Heteroarenes are employed as the amine source. This transformation provides a rapid and concise access to multifunctional imidazo[1,5-a]pyridines.

Entities: Chemical Species

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Year: 2014 PMID： 25415390 DOI： 10.1021/ol503165b

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

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Cited

7 in total

Review 1. Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage.

Authors: Gagandeep Kour Reen; Ashok Kumar; Pratibha Sharma
Journal: Beilstein J Org Chem Date: 2019-07-19 Impact factor: 2.883

2. Design and Exploration of Catalytic Activity of Two-Dimensional Surface-Engineered Graphene Oxide Nanosheets in the Transannulation of N-Heterocyclic Aldehydes or Ketones with Alkylamines.

Authors: Rakesh K Sharma; Aditi Sharma; Shivani Sharma; Sriparna Dutta; Sneha Yadav; Bhavya Arora
Journal: ACS Omega Date: 2019-02-12

3. Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes.

Authors: Dmitrii A Aksenov; Nikolai A Arutiunov; Vladimir V Maliuga; Alexander V Aksenov; Michael Rubin
Journal: Beilstein J Org Chem Date: 2020-11-26 Impact factor: 2.883

4. Electrochemical [4 + 1] Tandem sp³(C-H) Double Amination for the Direct Synthesis of 3-Acyl-Functionalized Imidazo[1,5-a]pyridines.

Authors: Qiang Wang; Xia Yao; Xian-Jing Xu; Shuai Zhang; Lei Ren
Journal: ACS Omega Date: 2022-01-27

Cu(I)-catalyzed transannulation of N-heteroaryl aldehydes or ketones with alkylamines via C(sp3)-H amination.

Review 1. Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage.

2. Design and Exploration of Catalytic Activity of Two-Dimensional Surface-Engineered Graphene Oxide Nanosheets in the Transannulation of N-Heterocyclic Aldehydes or Ketones with Alkylamines.

3. Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes.

4. Electrochemical [4 + 1] Tandem sp³(C-H) Double Amination for the Direct Synthesis of 3-Acyl-Functionalized Imidazo[1,5-a]pyridines.

5. The synthesis of imidazo[1,5-a]quinolines via a decarboxylative cyclization under metal-free conditions.

6. Mg₃N₂-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine.

7. Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.

Cu(I)-catalyzed transannulation of N-heteroaryl aldehydes or ketones with alkylamines via C(sp3)-H amination.

Review 1. Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage.

2. Design and Exploration of Catalytic Activity of Two-Dimensional Surface-Engineered Graphene Oxide Nanosheets in the Transannulation of N-Heterocyclic Aldehydes or Ketones with Alkylamines.

3. Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes.

4. Electrochemical [4 + 1] Tandem sp3(C-H) Double Amination for the Direct Synthesis of 3-Acyl-Functionalized Imidazo[1,5-a]pyridines.

5. The synthesis of imidazo[1,5-a]quinolines via a decarboxylative cyclization under metal-free conditions.

6. Mg3N2-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine.

7. Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.

4. Electrochemical [4 + 1] Tandem sp³(C-H) Double Amination for the Direct Synthesis of 3-Acyl-Functionalized Imidazo[1,5-a]pyridines.

6. Mg₃N₂-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine.