Categories: C-I Bond Formation >
Synthesis of α-iodoketones
Recent Literature
Under neutral reaction conditions, aromatic ketones were transformed into the
corresponding α-iodo ketones in high yields by the combination of copper(II)
oxide and iodine. Copper(II) oxide acts as catalyst to convert iodine into the
reactive iodonium ion and as a base to neutralize hydrogen iodide, and
reoxidizes iodide into molecular iodine.
G. Yin, M. Gao, N. She, S. Hu, A. Wu, Y. Pan, Synthesis, 2007,
3113-3116.
Selective introduction of an iodine atom at the α-carbonyl position in various
aryl alkyl ketones was effectively achieved by reaction of target molecules with
elemental iodine in the presence of N-F reagents such as F-TEDA-BF4 (Selectfluor)
as iodination mediators and methanol as the solvent.
M. Jereb, S. Stavber, M. Zupan, Synthesis,
2003, 853-858.
A direct asymmetric iodination reaction of aldehydes with NIS catalyzed by a
novel axially chiral bifunctional amino alcohol represents a rare example of a
highly enantioselective synthesis of optically active α-iodoaldehydes.
T. Kano, M. Ueda, K. Maruoka, J. Am. Chem. Soc., 2008,
130, 3728-3729.
Poly{[4-(hydroxy)(tosyloxy)iodo]styrene} was efficient in the halotosyloxylation
reaction of alkynes with iodine or NBS or NCS. The polymer reagent could be
regenerated and reused.
J.-M. Chen, X. Huang, Synthesis, 2004,
1557-1558.
