1,3-Dibromo-5,5-Dimethylhydantoin, DBDMH
DBDMH is a cheap and convenient alternative to NBS (N-bromosuccinimide) for example for the bromination of electron-rich arenes.
Recent Literature
A chiral bisoxazoline ligand/copper catalyst system mediates an asymmetric
oxidative desymmetrization of readily accessible 2-(hetero)aryl- and
alkyl-substituted glycerols with 1,3-dibromo-5,5-dimethylhydantoin and MeOH. The
present transformation provides straightforward access toward various glycerate
derivatives in good yields with high enantioselectivities.
K. Yamamoto, Y. Suganomata, T. Inoue, M. Kuriyama, Y. Demizu, O. Onomura, J. Org. Chem., 2022, 87,
6479-6491.
Organocatalytic stereospecific dibromination of various functionalized alkenes
was achieved using a simple thiourea catalyst and 1,3-dibromo
5,5-dimethylhydantoin as a stable, inexpensive halogen source at room
temperature. The procedure was extended to alkynes and aromatic rings and to
dichlorination reactions by using the 1,3-dichloro hydantoin derivative.
G. Hernández-Torres, B. Tan, C. F. Barbas III, Org. Lett., 2012,
14, 1858-1861.
A direct 1,2-dibromination of alkenes with 1,3-dibromo-5,5-dimethylhydantoin
(DBDMH) as bromine source proceeds under mild reaction conditions without the
use of a catalyst and an external oxidant. Various sorts of alkene substrates
are transformed into the corresponding 1,2-dibrominated products in good to
excellent yields and exclusive diastereoselectivity.
L. Wang, L. Zhai, J. Chen, Y. Gong, P. Wang, H. Li, X. She, J. Org. Chem., 2022, 87,
3177-3183.
Treatment of methylarenes with 1,3-dibromo-5,5-dimethylhydantoin or N-bromosuccinimide
and a catalytic amount of 2,2′-azobis(isobutyronitrile) followed by a reaction
with a nucleophile, such as benzoic acid, p-toluenethiol, sodium p-toluenesulfinate,
aqueous dimethylamine, or succinimide, provides the corresponding benzylated
products in good yields.
H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2015, 47,
1280-1290.
A catalytic decarboxylative halogenation of (hetero)aryl carboxylic acids
accommodates an exceptionally broad scope of substrates. The generated aryl
radical intermediate enables divergent functionalization pathways: (1) atom
transfer to access bromo- or iodo(hetero)arenes or (2) radical capture by copper
and subsequent reductive elimination to generate chloro- or
fluoro(hetero)arenes.
T. Q. Chen, P. Scott Pedersen, N. W. Dow, R. Fayad, C. E. Hauke, M. S. Rosko, E.
O. Danilov, D. C. Blakemore, A.-M. Dechert-Schmitt, T. Knauber, F. N. Castelano,
D. W. C. MacMillan, J. Am. Chem. Soc.,
2022, 144, 8296-8305.
A mild and efficient oxidation of various thiols affords the corresponding
disulfides using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as oxidant under both
solution and solvent-free conditions.
A. Khazaei, M. A. Zolfigol, A. Rostami, Synthesis,
2004, 2959-2961.
A mild and efficient method enables the formation of methylene acetals from 1,2-
and 1,3-diols using methoxymethylphenylsulfide,
1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT). The
use of BHT suppresses side reactions and enables high-yielding formation of
methylene acetals of various diols, including carbohydrate-type substrates.
T. Maegawa, Y. Koutani, K. Otake, H. Fujioka, J. Org. Chem., 2013,
78, 3384-3390.
An oxidative rearrangement of 3-aminoindazoles provides diversely
functionalized 1,2,3-benzotriazine-4(3H)-ones in good yields at room
temperature. Water as cosolvent facilitates the halogen-induced ring expansion
of 3-aminoindazoles under oxidative conditions.
Y. Zhou, Y. Wang, Y. Lou, Q. Song, Org. Lett.,
2018, 20, 6494-6497.
