Categories: C-Br Bond Formation >
Synthesis of bromohydrins
Recent Literature
Highly regioselective ring opening of epoxides to halohydrins has been
carried out in impressive yields with hydrogen and lithium halides in presence
of β-cyclodextrin using water as solvent.
M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron,
2002, 58, 6003-6008.
The use of trihaloisocyanuric acid/triphenylphosphine enables a regioselective
conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides
under mild and neutral conditions in acetonitrile. The reactions proceed
smoothly in high yield at room temperature and at reflux, respectively, over a
short time.
V. S. C. de Andrade, M. C. S. de Mattos,
Synthesis, 2016, 48, 1381-1388.
A very rapid and efficient method has been developed for the synthesis of
vicinal bromohydrins and alkoxybromides directly from olefins without any
catalyst using N,N-dibromo-p-toluenesulfonamide (TsNBr2)
as the brominating agent in CH3CN-water or alcohol.
P. Phukan, P. Chakraborty, D. Kataki, J. Org. Chem., 2006,
71, 7533-7537.
A very rapid and efficient method has been developed for the synthesis of
vicinal bromohydrins and alkoxybromides directly from olefins without any
catalyst using N,N-dibromo-p-toluenesulfonamide (TsNBr2)
as the brominating agent in CH3CN-water or alcohol.
P. Phukan, P. Chakraborty, D. Kataki, J. Org. Chem., 2006,
71, 7533-7537.
A visible-light metal-free photocatalytic regioselective and enantioselective
alkene halofunctionalization reaction of various terminal and internal alkenes
provides α-halogenated and α,β-dibrominated derivatives in good to excellent
yields within reaction time as short as 5 min. Different types of products can
be obtained by adjusting the reaction conditions.
H. Li, J. Fu, J. Fu, X. Li, D. Wei, H. Chen, L. Bai, L. Yang, H. Yang, W.
Wang, J. Org. Chem., 2023, 88,
6911-6917.
A zwitterion-catalyzed intermolecular bromoesterification of alkenes works
with acid and olefin in an equimolar ratio. Mechanistic study revealed that the
charge pair in the zwitterion works synergistically in activating both NBS and
carboxylic acid.
W.-H. Ng, R.-B. Hu, Y.-P. Lam, Y.-Y. Yeung,
Org. Lett., 2020, 22, 5567-5571.
Electrochemical technology enables alkene alkoxyhalogenation and organohalide
dehalogenation in one pot. Anodic conversion of the C=C bond to radical cation
intermediates and cathodic transformations of organohalides run in parallel.
T.-T. Zhang, M.-J. Luo, Y. Li, R.-J. Song, J.-H. Li,
Org. Lett., 2020, 22, 7230-7233.
The reaction of tribromoisocyanuric acid with alkenes in the presence of
nucleophilic solvents (various alcohols, acetic acid, and H2O in
acetone) led to the corresponding β-bromoethers, β-bromoacetates and
bromohydrins in high regioselectivity and good yields.
L. S. de Almeida, P. M. Esteves, M. C. S. de Mattos, Synlett,
2006, 1515-1518.
A green, oxidant-free electrochemical method enables radical bromination,
chlorination and trifluoromethylation-formyloxylation of various alkenes with
readily available halogen radical (NaCl, NaBr), and trifluoromethyl radical (CF3SO2Na)
sources in DMF as formyloxylation reagent in an undivided electrochemical cell.
X. Sun, H.-X. Ma, T.-S. Mei, P. Fang, Y. Hu,
Org. Lett., 2019, 21, 3167-3171.
Oxidative
bromination of different types of olefins using Selectfluor/KBr afforded addition,
monobromo-substituted, or Hunsdiecker-Borodin reaction products in good yields.
C. Ye, J. M. Shreeve, J. Org. Chem.,
2004,
69, 8561-8563.