Synthesis and reactivity of new strained cyclic allene and alkyne precursors*
Diego Peña, Beatriz Iglesias, Iago Quintana, Dolores Pérez, Enrique Guitián, and Luis Castedo
Departamento de Química Orgánica, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Abstract: The synthesis of ortho-(trimethylsilyl)vinyl triflates is described. Fluoride-induced decomposition of these triflates leads to the generation of strained cycloallenes and cycloalkynes under mild reaction conditions. The generation rate of these highly reactive intermediates can be modulated by modifying the solubility of the fluoride source. The slow generation of cyclic allenes and alkynes is a prerequisite for their use in homogeneous catalysis.
Keywords: cyclic allenes; cycloalkynes; catalysis; palladium; benzyne.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.