Methodologies for selective electrophilic fluorination

Abstract

Chapter 1 Chapter 1 contains a discussion of the effects of the introduction of fluorine atoms into organic molecules. A review of electrophilic fluorination reactions which have been reported recently, from the viewpoint of selectivity is given. Chapter 2 As a new methodology for selective fluorination of unactivated C-H sites, geometrically directed remote fluorination of steroid derivatives was investigated. Steroid derivatives bearing a variety of tethers which possess an ability to interact with elemental fluorine were prepared. Direct fluorination of 3ɑ-(3-cyanobenzoyloxy)- 5ɑ-androstan-17-one showed an increased selectivity for the 9-position compared with the control reactions. Chapter 3 A feasibility study of the use of elemental fluorine for catalytic enantioselective fluorination reaction of 1,3-ketoesters was conducted. A range of metal compounds were examined in the fluorination of a 1,3-ketoester and some of them were applied for further investigation involving attempts at catalytic enantioselective direct fluorination. Chapter 4 The capability of the Durham-type multi-channel microreactor for direct fluorination of carbonyl compounds was demonstrated. Effects of various parameters on the conversion and the selectivity in the direct fluorination of ethyl 3-oxobutanoate using a 9-channel microreactor were investigated systematically and results were helpful for determining the conditions of fluorination of other substrates. Chapter 5 Some miscellaneous reactions were collected in this chapter Chapter 6-9 Experimental details of the work discussed in Chapter 2-5.