Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Direct amination of azoles via catalytic C-H, N-H coupling.

Literature DB >> 19254040

Direct amination of azoles via catalytic C-H, N-H coupling.

Daiki Monguchi¹, Taiki Fujiwara, Hirotoshi Furukawa, Atsunori Mori.

Abstract

C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.

Entities: Chemical

Year: 2009 PMID： 19254040 DOI： 10.1021/ol900298e

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

Keyword Cloud
Cited

22 in total

Review 1. Aerobic copper-catalyzed organic reactions.

Authors: Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal: Chem Rev Date: 2013-06-20 Impact factor: 60.622

2. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

Authors: Jun Pan; Mingjuan Su; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-08-02 Impact factor: 15.336

3. Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.

Authors: Abhishek A Kantak; Shathaverdhan Potavathri; Rose A Barham; Kaitlyn M Romano; Brenton DeBoef
Journal: J Am Chem Soc Date: 2011-11-16 Impact factor: 15.419

4. Regioselective C-H bond amination by aminoiodanes.

Authors: Abhishek A Kantak; Louis Marchetti; Brenton DeBoef
Journal: Chem Commun (Camb) Date: 2015-02-28 Impact factor: 6.222

5. Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors: Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal: J Am Chem Soc Date: 2017-08-14 Impact factor: 15.419

6. First cascade Mitsunobu reactions for the synthesis of 2-benzoxazole-N-phenyl and 2-benzimidazole-N-phenyl derivatives.

Authors: Yu Yan; Qifei Zhong; Nan Zhao; Gang Liu
Journal: Mol Divers Date: 2011-11-30 Impact factor: 2.943

Direct amination of azoles via catalytic C-H, N-H coupling.

Review 1. Aerobic copper-catalyzed organic reactions.

2. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

3. Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.

4. Regioselective C-H bond amination by aminoiodanes.

5. Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

6. First cascade Mitsunobu reactions for the synthesis of 2-benzoxazole-N-phenyl and 2-benzimidazole-N-phenyl derivatives.

7. Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

8. A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.

9. An aromatic Glaser-Hay reaction.

10. Copper-mediated amidation of heterocyclic and aromatic C-H bonds.