Song, Geyang, Nong, Ding-Zhan, Li, Qi, Yan, Yonggang, Li, Gang, Fan, Juan, Zhang, Wei, Cao, Rui, Wang, Chao, Xiao, Jianliang ORCID: 0000-0003-2010-247X et al (show 1 more authors)
(2022)
Photochemical Synthesis of Anilines via Ni-Catalyzed Coupling of Aryl Halides with Ammonium Salts.
ACS CATALYSIS, 12 (24).
pp. 15590-15599.
Text
Manuscript-Aryl Halides Coupling with Ammonium Salts AAM.pdf - Author Accepted Manuscript Download (1MB) | Preview |
Abstract
Easy, efficient, and economic synthesis of anilines remains an important challenge in synthetic chemistry. In this study, a Ni(OAc)2-bipyridine complex is shown to readily catalyze the amination of aryl halides with ammonium salts under direct excitation of light, allowing a broad array of aryl chlorides and bromides to be converted into the corresponding primary (hetero)arylamines in the absence of an external photosensitizer. Late-stage modification of drug molecules and 15N-labeling of primary aryl amines are also demonstrated with a number of examples. Photoinduced generation of Ni(I)-bipyridine species is believed to be the key step in the reaction, enabling a Ni(I)/Ni(III) cycle for catalytic turnover.
Item Type: | Article |
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Uncontrolled Keywords: | C-N coupling, ammonium salt, primary amines, aryl halides, nickel catalysis |
Divisions: | Faculty of Science and Engineering > School of Physical Sciences |
Depositing User: | Symplectic Admin |
Date Deposited: | 19 Apr 2023 09:00 |
Last Modified: | 05 Dec 2023 02:30 |
DOI: | 10.1021/acscatal.2c04959 |
Related URLs: | |
URI: | https://livrepository.liverpool.ac.uk/id/eprint/3169720 |