Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent.
The use of bis(pyridine)iodonium tetrafluoroborate (IPy(2)BF(4)) as an oxidizing agent towards different types of alcohols is reported. The observed reactivity involves different reaction pathways, as a function both of the structures of the starting materials and of the experimental conditions. Interestingly, the title iodine-containing compound is capable of a tuneable reaction with simple cycloalkanols, providing straight and selective access either to omega-iodocarbonyl compounds or to ketones, a previously unreported and chemoselective range of oxidation potential. Furthermore, appropriate conditions for the preparation of aldehydes and esters from primary alcohols by easily performed experimental procedures were also established. The beta-scission reactions of cycloalkanols and the alpha-oxidation processes of primary, secondary and benzylic alcohols are discussed.
Barluenga
José
J
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain. barluenga@uniovi.es
González-Bobes
Francisco
F
Murguía
Marcelo C
MC
Ananthoju
Sreenivasa R
SR
González
José M
JM