Citation: Xiao-Bo Liu, Ren-Ming Liu, Xiao-Di Bao, Hua-Jian Xu, Qi Zhang, Yu-Feng Liang. Nickel-catalyzed reductive formylation of aryl halides via formyl radical[J]. Chinese Chemical Letters, ;2024, 35(12): 109783. doi: 10.1016/j.cclet.2024.109783 shu

Nickel-catalyzed reductive formylation of aryl halides via formyl radical

Xiao-Bo Liu ^{a, c} ,
Ren-Ming Liu ^c ,
Xiao-Di Bao ^c ,
Hua-Jian Xu ^{a, *,} ,
Qi Zhang ^{b, *,} ,
Yu-Feng Liang ^{c, *,}

a.
School of Food and Biological Engineering, School of Chemistry and Chemical Engineering, Anhui Province Key Laboratory of Advance Catalytic Materials and Reaction Engineering, Hefei University of Technology, Hefei 230009, China
b.
Institute of Industry & Equipment Technology, Hefei University of Technology, Hefei 230009, China
c.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China

hjxu@hfut.edu.cn

zhangq@hfut.edu.cn

yfliang@sdu.edu.cn

Received Date: 29 November 2023
Revised Date: 2 March 2024
Accepted Date: 15 March 2024
Available Online: 20 March 2024

Figures(6)

Aromatic aldehydes are the most fundamentally important compounds used in organic synthesis. The development of new synthetic methods for introduction of a formyl group into an organic scaffold is highly desirable. In this report, a nickel-catalyzed reductive coupling between aryl halides and α–chloro N-methoxyphthalimide has been documented for the synthesis of a diverse array of aromatic aldehydes. Because of mild reductive coupling conditions, excellent functional group tolerance, especially for substrates containing free -OH and -NH₂, was observed. Due to the simple operation mode, a large library of aromatic aldehydes can be quickly constructed by this process. Moreover, the present protocol is amenable for late-stage functionalization of bioactive compound. A combined computational and experimental investigation suggested the reaction may undergo a reaction mechanism of active Ni(I) catalyst formation and the formation of key formyl radical intermediate under zinc reductive conditions.
- Nickel,
- Formylation,
- Radical,
- SET,
- Reductive coupling
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沈阳化工大学材料科学与工程学院沈阳 110142