Photochemical Synthesis of Anilines via Ni-Catalyzed Coupling of Aryl Halides with Ammonium Salts



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.

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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
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