Citation: Chunyang Hu, Fangming Chen, Guo-Ping Lu, Wen-Bin Yi. Deuterated N-difluoromethylthiophthalimide: A stable, scalable reagent for radical and electrophilic deuteriodifluoromethylthiolations[J]. Chinese Chemical Letters, ;2022, 33(9): 4293-4297. doi: 10.1016/j.cclet.2022.01.013 shu

Deuterated N-difluoromethylthiophthalimide: A stable, scalable reagent for radical and electrophilic deuteriodifluoromethylthiolations

Chunyang Hu ^a ,
Fangming Chen ^a ,
Guo-Ping Lu ^{a, *,} ,
Wen-Bin Yi ^{a, b, **,}

a.
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
b.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

^**

glu@njust.edu.cn

yiwb@njust.edu.cn

Received Date: 4 November 2021
Revised Date: 6 January 2022
Accepted Date: 6 January 2022
Available Online: 13 January 2022

Figures(9)

A new, stable and scalable reagent for deuteriodifluoromethylthiolation (deuterated N-difluoromethylthiophthalimide, PhthSCF₂D) has been developed. This reagent can be applied for the photocatalytic radical deuteriodifluoromethylthiolation of various olefins and aldehydes (30 examples). Meanwhile, it can achieve the electrophilic deuteriodifluoromethylthiolation of a series of electrophilic substrates including electron-rich arenes, aryl/vinylboronicacids, alkynes, amines, thiols and β-ketoesters (22 examples). Some complex molecules can also be applied in both radical and electrophilic deuteriodifluoromethylthiolation using PhthSCF₂D as the reagent.
- Deuteration,
- Deuteriodifluoromethylthiolation,
- Photocatalytic,
- Electrophilic,
- Radical
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