Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 14627-14639Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01467
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Funding
- Hubei Key Laboratory of Catalysis and Materials Science [CHCL19002]
- Innovation Team Cultivation Fund of Hubei University of Arts and Sciences [2020kypyt004]
- National Undergraduate Innovation and Entrepreneurship Training Program [201910519006]
- Foundation of Hubei University of Arts and Science [2059057]
- Scientific Research Program Guiding Project of Hubei Provincial Department of Education [B2019135]
- Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education
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A metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, yielding numerous heteroaryl amines or their hydrochlorides without the need for any external base. The basicity of amines and specific interactions derived from X-ray crystallography analysis played pivotal roles in the reactions. The protocol was scalable to gram scales and applicable to drug molecules, demonstrating its practical value for further applications.
Herein, a metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, which afforded numerous heteroaryl amines or their hydrochlorides without any external base. Further investigations elucidated that the basicity of amines and specific interactions derived from the X-ray crystallography analysis of 3j'center dot HCl played pivotal roles in the reactions. Moreover, this protocol was scalable to gram scales and applicable to drug molecules, which demonstrated its practical value for further applications.
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