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Bis(pyridine)iodonium Tetrafluoroborate (IPy 2 BF 4 ): A Versatile Oxidizing Reagent
Author(s) -
Barluenga José,
GonzálezBobes Francisco,
Murguía Marcelo C.,
Ananthoju Sreenivasa R.,
González José M.
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400136
Subject(s) - tetrafluoroborate , oxidizing agent , reagent , pyridine , chemistry , alcohol oxidation , reactivity (psychology) , alcohol , bond cleavage , organic chemistry , primary (astronomy) , combinatorial chemistry , medicinal chemistry , catalysis , ionic liquid , medicine , alternative medicine , physics , pathology , astronomy
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 ω‐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 β‐scission reactions of cycloalkanols and the α‐oxidation processes of primary, secondary and benzylic alcohols are discussed.