1. 1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides
Fei-Fei Xu, Claney L Pereira, Peter H Seeberger Beilstein J Org Chem. 2017 Sep 22;13:1994-1998.doi: 10.3762/bjoc.13.195.eCollection 2017.
1,3-Dibromo-5,5-dimethylhydantoin (DBDMH), an inexpensive, non-toxic and stable reagent, is a competent activator of thioglycosides for glycosidic bond formation. Excellent yields were obtained when triflic acid (TfOH) or trimethylsilyl trifluoromethanesulfonate (TMSOTf) were employed as co-promoters in solution or automated glycan assembly on solid phase.
2. 1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
Chunhua Ma, Guojie Fan, Ping Wu, Zhi Li, Yang Zhou, Qingjie Ding, Wei Zhang Org Biomol Chem. 2017 Nov 29;15(46):9889-9894.doi: 10.1039/c7ob02329d.
A variety of terminal alkenes were converted to the corresponding amides in yields of 25 to 86% in water via treatment with 1,3-dibromo-5,5-dimethylhydantoin, followed by reaction with molecular iodine and aq. NH3 (or amine) in one pot. This metal- and organic solvent-free protocol is not only suitable for styrene derivatives, but also, for the first time, works well on terminal aliphatic alkenes.
3. Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source
Lei Wang, Lele Zhai, Jinyan Chen, Yulin Gong, Peng Wang, Huilin Li, Xuegong She J Org Chem. 2022 Mar 4;87(5):3177-3183.doi: 10.1021/acs.joc.1c02906.Epub 2022 Feb 8.
A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction 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 with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.
