105494-81-3Relevant articles and documents
Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates
Talko, Alicja,Antoniak, Damian,Barbasiewicz, Micha?
, p. 2278 - 2286 (2019)
Studies on directed ortho -metalation (DoM) of arenesulfonyl fluorides (ArSO 2 F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, -78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO 2 F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO 2 F) display fragmentation to arynes and migration of the SO 2 F group to the ortho position (anionic thia-Fries rearrangement).