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. Author manuscript; available in PMC: 2017 Sep 7.
Published in final edited form as: J Am Chem Soc. 2016 Aug 26;138(35):11360–11367. doi: 10.1021/jacs.6b07221

Table 2.

Structure–Reactivity Relationship Studies of Nucleophilic Fluorination Reagents

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entrya variation from the std conditions observations
1 replace Et3N·3HF with Et3N·HF, Et3N·2HF, TBAF(tBuOH)4, or AgF decomposition of 2d, no desired product
2 replace XtalFluor-E with XtalFluor-M 3d (65%) with full conversion
3 replace Et3N·3HF/XtalFluor-E with benzoyl fluoride 3d (<5%) with 66% conversionb
4 replace Et3N·3HF/XtalFluor-E with DFI or PhenoFluor decomposition of 2d, no desired product
5 replace Et3N·3HF/XtalFluor-E with DAST decomposition of 2d, no desired product
6 replace Et3N·3HF/XtalFluor-E (1.5 equiv/2.5 equiv) with DAST/XtalFluor-E (1.5 equiv/ 1.0 equiv) 3d (51%) with full conversion
a

Reactions were carried out under N2 at −15 °C in 2 h, and 4 Å activated molecular sieves (powder) were used to remove deleterious moisture, unless stated otherwise.

b

Amino-oxygenation product 4d (42%) and benzoylated 2d (24%) were isolated.