Difluoromethyl 2-Pyridyl Sulfone: A New gem-Difluoroolefination Reagent for Aldehydes and Ketones

Yanchuan Zhao, Weizhou Huang, Lingui Zhu and Jinbo Hu*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China, Email: jinbohusioc.ac.cn

Y. Zhao, W. Huang, L. Zhu, J. Hu, Org. Lett., 2010, 12, 1444-1447.

DOI: 10.1021/ol100090r

---

Abstract

Difluoromethyl 2-pyridyl sulfone acts as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. A fluorinated sulfinate intermediate in the reaction is relatively stable and can be observed by ¹⁹F NMR and trapped with CH₃I.

see article for more examples

proposed mechanism

---

---

Copper-Catalyzed gem-Difluoroolefination of Diazo Compounds with TMSCF₃ via C-F Bond Cleavage

M. Hu, Z. He, B. Gao, L. Li, C. Ni, J. Hu, J. Am. Chem. Soc., 2013, 135, 17302-17305.

---

Key Words

Alkenyl Halides, Julia-Kocienski Olefination

---

ID: J54-Y2010-0870