Citation: Qi-Ying Liao, Chao Ma, Yu-Chao Wang, Shao-Qian Yang, Jiang-Shan Ma, Zhi-Tao He. Enantioselective and stereodivergent hydromonofluoroalkylation of conjugated and remote dienes[J]. Chinese Chemical Letters, ;2023, 34(12): 108371. doi: 10.1016/j.cclet.2023.108371 shu

Enantioselective and stereodivergent hydromonofluoroalkylation of conjugated and remote dienes

Qi-Ying Liao ^{a, b, 1} ,
Chao Ma ^{b, 1} ,
Yu-Chao Wang ^b ,
Shao-Qian Yang ^b ,
Jiang-Shan Ma ^b ,
Zhi-Tao He ^{a, b, c, *,}

a.
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, China
b.
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China
c.
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China

^☆

hezt@sioc.ac.cn

Received Date: 21 December 2022
Revised Date: 18 March 2023
Accepted Date: 22 March 2023
Available Online: 23 March 2023

Figures(6)

Because of the widespread applications of optically active alkyl fluorides in medicinal and agro chemicals, enantioselective and even stereodivergent construction of alkyl fluorides remains highly desirable but underdeveloped. Transition-metal-catalyzed asymmetric hydrofluoroalkylation of readily available dienes represents a novel route to achieve this goal, yet receives scarce study. Here we report an intriguing palladium-catalyzed enantioselective hydromonofluoroalkylation reaction of conjugated dienes. Both monosubstituted and internal dienes proceed well with the transformation and furnish alkyl fluorides in generally > 80% yield and > 90% ee. A stereodivergent hydromonofluoroalkylation protocol via Pd/Cu co-catalysis is also established for the access to all four stereoisomers of corresponding moieties bearing a fully-substituted F-stereogenic center and vicinal tertiary carbon center. In addition, asymmetric migratory hydromonofluoroalkylation of skipped dienes is developed to realize the direct allylic CH fluoroalkylation. A compound library of enantioenriched cyclic fluorides is thus built to highlight the transformation potential of present methodology.
- Hydromonofluoroalkylation,
- Enantioselective,
- Stereodivergent,
- 1,3-Diene,
- Remote diene
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沈阳化工大学材料科学与工程学院沈阳 110142