Categories: C-Br Bond Formation >
Synthesis of β-Bromoketones
Recent Literature
A simple electrochemical protocol for the preparation of 2-bromoethyl- and
2-iodoethyl ketones from cyclopropanols and magnesium halides proceeds with
exclusive regioselectivity and without epimerization of the α-stereocenter in
the products. 2-bromoethyl ketones undergo smooth copper and nickel-catalyzed
alkylation, alkenylation, and arylations reactions.
M. V. Barysevich, Y. M. Aniskevich, A. L. Hurski, Synlett, 2021,
32,
1934-1938.
A mild oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium
nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides β-functionalized
ketones in short reaction times. This method provides an alternative
pathway to important starting materials and intermediates in organic synthesis.
J. Jiao, L. X. Nguyen, D. R. Patterson, R. A. Flowers II, Org. Lett., 2007,
9, 1323-1326.
Treatment of vinyl ketones with a combination of TiCl4 and n-Bu4NI
followed by an addition of a variety of aldehydes provides syn-α-iodomethyl-β-hydroxy
ketones with high stereoselectivity. The use of n-Bu4NBr or
n-Bu4NCl provides the corresponding bromo or chloro compounds in
good yields.
Z. Han, S. Uehira, H. Shinokubo, K. Oshima, J. Org. Chem., 2001,
66, 7854-7857.
