The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded fluorinated azaxanthones or biaryls. The [4+2] cycloaddition of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy)-1,3-diene with DMAD afforded dimethyl 4-fluoro-3,5-dihydroxyphthalate. Various arylated phthalates, naphthoates, indoles, are synthesized Pd(0)-catalyzed Suzuki cross-coupling reaction and studied. The experimental and theoretical study of the silylium arene adducts ([Me3Si-Ar][B(C6F5)4]) and the catalytic trimerisation of bissilylated diazomethane are studied.