Silylated allenes as precursors of fluorinated dienes and propargylic fluorides

ORGN 134

Mª Carmen Pacheco, maria.pacheco@chem.ox.ac.uk, Ludivine Garcia, sergentludi@hotmail.com, and Véronique Gouverneur, veronique.gouverneur@chem.ox.ac.uk. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom
The development of novel reactions for the preparation of fluorinated compounds, such as fluorinated drugs, is still in demand. We have demonstrated that the electrophilic fluorodesilylation of organosilanes featuring a silyl group attached or adjacent to a π system afforded various fluorinated products. Using this methodology, we have prepared fluoroalkenes and allylfluorides from the corresponding vinyl- and allylsilanes respectively. More recently, we have examined the reactivity of two classes of allenylsilanes upon treatment with an electrophilic source of fluorine. We found that allenylmethylsilane can be converted into fluorodienes. Propargylic fluorides featuring a fluorinated stereogenic centre can also be made available upon fluorodesilylation of the corresponding known allenylsilanes. This synthetic route toward propargylic fluorides is unprecedented and complements existing approaches to these valuable compounds. The preparation of various allenylsilanes and their conversion into either fluorodienes or propargylic fluorides will be reported.