52777-73-8Relevant articles and documents
Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source
Wang, Lei,Zhai, Lele,Chen, Jinyan,Gong, Yulin,Wang, Peng,Li, Huilin,She, Xuegong
supporting information, p. 3177 - 3183 (2022/02/23)
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.
A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions
Qi, Zaojuan,Li, Weihe,Niu, Yanning,Benassi, Enrico,Qian, Bo
supporting information, p. 2399 - 2404 (2021/03/03)
A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.
Enantiospecific on-water bromination: A mild and efficient protocol for the preparation of alkyl bromides
Alletto, Francesco,Adamo, Mauro F. A.
supporting information, p. 8692 - 8698 (2020/12/29)
Herein we report the first example of an on-water enantiospecific synthesis of alkyl bromides. This procedure allowed the conversion of secondary activated alkyl sulphides to benzylic alkyl bromides, which were obtained in 80-99% yields. The reaction carried out on enantio-pure sulphides provided the corresponding bromides in high yields and enantioselectivity (up to 92% ee; 94% es) at room temperature. The on-water conditions reduced significantly the reaction times compared to similar procedures run in organic media. The condition identified made use of no solvent, required no temperature control and produced a smooth organic phase easily separated for further synthetic use on a multigram-scale without the need for any organic extraction. Therefore, the present constitutes the most operationally simple and environmentally benign approach to a class of much sought organic intermediates. This journal is
