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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.
A general, rapid, and scalable method for the preparation of α-halogenated
ketones using N-alkenoxypyridinium salts as substrates and quaternary ammonium
salts as halogen sources offers mild reaction conditions,
excellent functional group tolerance, and a wide substrate
scope.
N. Wu, M. Jiang, A. Cao, L. Huang, X. Bo, Z. Xu, J. Org. Chem., 2023, 88,
17368-17380.
By utilizing N-heterocyclic carbenes as stabilizer through electrostatic
interaction rather than electron donation, a visible-light-triggered radical-radical cross-coupling of
N-alkenoxypyridinium salts and NaI provides a variety of α-iodo ketones.
H. Sheng, Q. Liu, X.-D. Su, Y. Lu, Z.-X. Wang, X.-Y. Chen,
Org. Lett., 2020, 22, 7187-7192.
An efficient approach to α,β-unsaturated α′-iodo ketones directly from
α,β-unsaturated ketones by selective iodination at the α′-position in the
presence of copper(II) oxide/iodine offers high yields, short reaction times,
inexpensive reagents, mild reaction conditions, ease of manipulation, and the
formation of cleaner products.
Z. Wang, G. Yin, J. Qin, M. Gao, L. Cao, A. Wu, Synthesis, 2008,
3565-3568.
Primary, secondary, tertiary, benzylic, propargylic and α-functionalized
alkyl fluorides react in chlorinated or aromatic solvents at room temperature or
upon heating with inexpensive lithium iodide to give the corresponding iodides
in very good yields. The reaction is selective for aliphatic monofluorides and
can be coupled with in situ nucleophilic iodide replacements.
K. Balaraman, S. Kyriazakos, R. Palmer, F. Y. Thanzeel, C. Wolf, Synthesis, 2022, 54,
4320-4328.
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.
Related
Sodium benzene sulfinate catalyzed a visible-light-driven aerobic oxidative
cleavage of olefins to provide the corresponding aldehydes and ketones under
transition-metal-free conditions. Notably, α-halo-substituted styrenes proceeded
with photoinduced oxidation to finally afford α-halo-acetophenones with halogen
migration.
Y.-X. Chen, J.-T. He, M.-C. Wu, Z.-L. Liu, K. Tang, P.-J. Xia, K. Chen, H.-Y.
Xiang, X.-Q. Chen, H. Yang, Org. Lett.,
2022, 24, 3920-3925.