Mild allylic defluorination of 3,3-difluorobut-1-ene derivative activated by a phenylsulfonyl group

作者：Hong Youn Young; Kim Ju Hee; Choi Su Jeong; Jeong In Howa^*

来源：Journal of Fluorine Chemistry, 2013, 155: 83-88.

DOI：10.1016/j.jfluchem.2013.06.011

• Allylic defluorination reaction
• 3-Alkylated 3,3-difluoropropenes
• Phenylsulfonyl group
• Monofluoroalkenes

4-Benzyloxy-3,3-difluoro-4-phenyl-2-phenylsulfonylbut-1-ene (3) underwent the allylic defluorination reaction with aryl- and alkylthiolate, and alkoxides without any additive reagents to give the monofluoroalkenes 4-5 in good yields. Reactions of 3 with various Grignard reagents such as alkyl-, aryl0, vinyl- and alkylethynylmagnesium bromides also provided the corresponding monofluoroalkenes 6 in good yields. Finally, compound 3 was reacted with -butylamine at -45 degrees C for 1 h to afford the monofluoroalkene 9 in good yields.

• 出版日期2013-11