Organic Chemistry Portal
Chemicals >> Oxidizing Agents

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.