Categories: C-I Bond Formation >
Synthesis of benzyl iodides
Recent Literature
The use of a CeCl3·7H2O/NaI system in acetonitrile enables an exceedingly mild preparation
of iodides from alcohols. The simplicity of this approach, the low cost of
reagents, and the ease of use display the attractiveness of the present method
for a wide variety of alcohols.
M. Di Deo, E. Marcantoni, E. Torregiani, G. Bartoli, M. C. Bellucci, M.
Bosco, L. Sambri, J. Org. Chem., 2000,
65, 2830-2833.
Silicaphosphine (Silphos), [P(Cl)3−n(SiO2)n] is a new
heterogeneous reagent that converts alcohols and thiols to their corresponding
bromides and iodides in the presence of molecular halogen in refluxing CH3CN
in high to quantitative yields. Separation of the Silphos oxide byproduct can be
achieved by a simple filtration.
N. Iranpoor, H. Firouzabadi, A. Jamalian, F. Kazemi, Tetrahedron, 2005,
61, 5699-5704.
The combination of Ph3P and easily available 1,2-dihaloethanes (XCH2CH2X; X =
Cl, Br, or I), was very effective for a mild deoxygenative halogenation of
alcohols and aldehydes. The use of (EtO)3P instead of Ph3P
enables a convenient purification process, as the byproduct (EtO)3P═O
could be removed by aqueous washing. A dehydroxy-fluorination proceeds well in
the presence of ICH2CH2I and CsF as fluoride source in DMF.
J. Chen, J.-H. Lin, J.-C. Xiao, Org. Lett.,
2018, 20, 3061-3064.
The use of H3PO3/I2 enables a reductive
iodination of various aromatic aldehydes to produce benzyl iodides. The benzyl
iodides can be converted into diarylmethanes or cyclic compounds in good yields
via in situ Friedel-Crafts type reactions.
F. Lv, J. Xiao, J. Xiang, F. Guo, Z.-L. Tang, L.-B. Han, J. Org. Chem., 2021, 86,
3081-3088.
Anhydrous hydrogen iodide preparated directly from molecular hydrogen and
iodine using a rhodium catalyst is highly active in the transformations of
alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding
iodoalkanes. Therefore, the present methodology offers a practical
method for the preparation of various iodoalkanes in excellent atom economy.
C. Zeng, G. Shen, F. Yang, J. Chen, X. Zhang, C. Gu, Y. Zhou, B. Fan, Org. Lett.,
2018, 20, 6859-6862.
An acid-mediated electrophilic hydrazinative halogenation of alkenes proceeds
with readily available diethyl azodicarboxylate as a hydrazine source and
low-cost potassium halides as nucleophilic halogen sources. A series of
iodinated, brominated, and chlorinated hydrazines are facilely produced with a
wide range of functional groups.
N. Huang, L. Liao, X. Zhao, Org. Lett., 2023, 25,
6587-6592.