A new catalytic Prins cyclization leading to oxa- and azacycles.
A new Prins cyclization process that builds up one carbon-carbon bond, one heteroatom-carbon bond, and one halogen-carbon bond, (in an oxa- and azacycle) relies on an iron catalyst system formed from Fe(acac)3 and trimethylsilyl halide. The method displays a broad substrate scope and is economical, environmentally friendly, and experimentally simple. This catalytic method permits the construction of chloro, bromo and iodo heterocycles, by the suitable combination of iron(III) source, the corresponding trimethylsilyl halide and the solvent, in high yields.
Miranda
Pedro O
PO
Instituto Universitario de Bio-Orgánica Antonio González Departamento de Química Orgánica, Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
Carballo
Rubén M
RM
Martín
Víctor S
VS
Padrón
Juan I
JI
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007501:Iron / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D012492:Salts; D014297:Trimethylsilyl Compounds; D007501:Iron