Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• fluorodesulfurizations of carbonyl derivatives using a combination of sources of halonium and fluoride ions such as 1,3-dibromo-5,5-dimethylhydantoin (DBH) and tetrabutylammonium dihydrogen trifluoride have been achieved [9][10][11]. The transformation of methylene to difluoromethylene using electrophilic fluorinating

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• mentioning that Hojati et al., in 2013, developed a simple, novel and efficient procedure for the synthesis of BIMs, utilizing 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as the catalyst (Scheme 3). DBDMH is an N-halo-reagent, which has found widespread applications in industrial processes, due to its economic

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• brominated imides, such as N-bromosuccinimide (NBS), N-bromosaccharin (NBSA), tribromoisocyanuric acid (TBCA), 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and so on (Scheme 1, reaction 2) [21][22][23][24]. However, reports on the bromination of C5–H of 8-aminoquinolines employing acyl bromides, alkyl bromides

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• 6.2.1 Double bond functionalisation: Singh et al. [56] developed a large-scale synthesis of methoxyiminostilbene 151, a precursor to the antidepressant oxcarbazepine (153). Bromination of acetyl-protected 1a by 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in methanol gives the bromohydrin ether 150 in

Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

• Carl Recsei and
• Yaniv Barda

Beilstein J. Org. Chem. 2021, 17, 813–818, doi:10.3762/bjoc.17.70

• %. Synthesis of 1. Reagents and conditions: (a) 1,3-dibromo-5,5-dimethylhydantoin, benzoyl peroxide, (CH2Cl)2, reflux, 4 h, 88%; (b) 5,5-dimethyl-3-(4H-isoxazolyl) carbamimidothioate·HCl, K2CO3, MeCN/H2O, 50 °C, 1.5 h, 73%; (c) H2O2, Na2WO4, MeCN/H2O, 45 °C, 1.5 d, 66%. Synthesis of 11–13. Reagents and

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• 3Aa or 3Aa’, the halocyclization of 2Aa with N-bromosuccinimide (NBS, 2.0 equiv)/BF3·Et2O (1.1 equiv), with 1,3-diiodo-5,5-dimethylhydantoin (DIH, 2.0 equiv)/BF3·Et2O (1.1 equiv), and with 1,3-dibromo-5,5-dimethylhydantoin (DBH, 2.0 equiv)/BF3·Et2O (1.1 equiv) was carried out to form 3-bromo-4

1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides

• Fei-Fei Xu,
• Claney L. Pereira and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2017, 13, 1994–1998, doi:10.3762/bjoc.13.195

• GmbH, Magnusstraße 11, 12489 Berlin, Germany 10.3762/bjoc.13.195 Abstract 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. Keywords: automated glycan assembly; 1,3-dibromo-5,5-dimethylhydantoin; glycosylation; promoter; thioglycosides; Introduction Thioglycosides are versatile glycosylating

• be freshly prepared prior to use [24][25][26]. Here, we describe a promoter system based on the commercially available, inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) for the activation of thioglycosides. DBDMH, a white to pale-brown powder that is readily soluble in most organic solvents

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds

• Nivesh Kumar,
• Santanu Ghosh,
• Subhajit Bhunia and
• Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

• , and 7) of products were observed with reactions being unclean (mixture of products) [54]. KOt-Bu was superior over other bases used in this reaction like NaH, NaOMe, K2CO3, Cs2CO3, and NaOt-Bu (Table 1, entries 9–13). Among other metal-free oxidants, iodosobenzenediacetate (PIDA), DBDMH (1,3-dibromo

• -5,5-dimethylhydantoin), and ICl afforded 2-oxindole 4a in 82%, 16%, and 69%, respectively (Table 1, entries 17–19). Later, we turned our attention to N-halo succinimides as potential oxidants in our methodology [53]. Interestingly, N-iodosuccinimide (NIS), N-bromosuccinimide (NBS), and N

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

• André S. Kelch,
• Peter G. Jones,
• Ina Dix and
• Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

• better leaving group, e.g. bromine as in Scheme 7. After trying numerous different protocols (Br2 addition, NBS in different concentrations and in different solvents, 1,3-dibromo-5,5-dimethylhydantoin) [14] we finally found that excess NBS (6 equivalents) and refluxing in tetrachloromethane at 80 °C gave

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• desulfurization-fluorination has been disclosed by Hiyama [24][25][26][27]. When dithiocarbonates (2, xanthogenates) are exposed to a huge excess of hydrogen fluoride-pyridine and 1,3-dibromo-5,5-dimethylhydantoin, trifluoromethyl ethers form in moderate to excellent yields (Scheme 5 and Table 5). What makes this