Categories: C-F Bond Formation >
Synthesis of fluorohydrins
Recent Literature
Fluorinations of epoxides and alkyl mesylates can be effectively achieved by
reaction with Et3N • 3 HFunder microwave irradiation. The
reactions were completed in a few minutes and the use of large excess of
reagents could be avoided.
T. Inagaki, T. Fukuhara, S. Hara, Synthesis,
2003, 1157-1159.
Related
An iridium-catalyzed hydrogenation of α-fluoro ketones provides β-fluoro
alcohols with good enantiomeric and diastereomeric selectivities using a
strategy of dynamic kinetic resolution. A C-F···Na charge-dipole interaction in
the transition state of hydride transfer is responsible for the diastereomeric
control.
X. Tan, W. Zeng, J. Wen, X. Zhang,
Org. Lett., 2020, 22, 7230-7233.
A direct and straightforward nucleophilic fluoromethylation of organic
compounds employs a very labile lithium fluorocarbenoid (LiCH2F)
generated from commercially available fluoroiodomethane. The versatility of the
strategy is showcased in reactions involving a plethora of electrophiles
providing highly valuable chemicals such as fluoroalcohols, fluoroamines, and
fluoromethylated oxygenated heterocycles in very good yields.
G. Parisi, M. Colella, S. Monticelli, G. Romanazzi, W. Holzer, T. Langer, L.
Degennaro, V. Pace, R. Luisi, J. Am. Chem. Soc., 2017,
139, 13648-13651.
A nickel-catalyzed enantioselective hydrofluoromethylation of enamides and
enol esters with ICH2F as the fluoromethyl source provides chiral
α-fluoromethylated amides as well as esters with wide functional group
compatibility as well as excellent enantioselectivity.
Y. Du, S. Chen, H. Cao, Y. Zhang, H. Lei, G. Xia, H. Huang, Z. Li, Org. Lett., 2023, 25,
2218-2222.