ABSTRACT
A free-radical mediated highly ordered radical addition/cyclization/(sp(3))C-C(sp(3)) formation domino reaction is developed. Three new C-C bonds are formed one by one in a mixed system. Furthermore, it represents the first example of cascade C-C bond formation via selective functionalization of α-hydroxyl-C(sp(3))-H in fluorinated alcohols.
ABSTRACT
A C-C formation of an electron-rich N-heterocycle with fluorinated alcohol is developed. Through this radical-triggered cross-dehydrogenative coupling strategy, a wide range of useful building blocks such as C3 hydroxyfluoroalkylated indoles and pyrroles can be site-specifically synthesized. Mechanistic studies indicate a single-electron-transfer initiated radical cycle would be involved.
ABSTRACT
A stereospecific decarboxylative silylation of acrylic and propiolic acids with silanes was developed. This reaction represents the first example of decarboxylative C-Si bond formation and provides an efficient and convenient approach to various synthetically useful alkenyl and alkynyl organosilicon compounds through the reaction of α,ß-unsaturated acids with silanes. Spin-trapping and EPR experiments support a radical addition/elimination process.
ABSTRACT
A scalable, selective, and operationally easy iodotrifluoromethylation of a wide range of alkenes and alkynes by using two simple and safe solids, sodium trifluoromethanesulfinate and iodine pentoxide, in aqueous medium has been developed. Mechanistic studies confirm that free-radical processes are involved in this system since the key radical intermediates such as CF(3) and ß-CF(3) alkyl radicals have been clearly detected by spin trapping and electron spin resonance.
