92-04-6Relevant articles and documents
Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/01/04)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds
Gao, Chao,Li, Hongchen,Liu, Miaochang,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue,Gao, Wenxia,Wu, Ge
, p. 46636 - 46643 (2017/10/16)
We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.
Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride
Yin, Zhiwei,Zhang, Jinzhu,Wu, Jing,Green, Riana,Li, Sihan,Zheng, Shengping
supporting information, p. 2854 - 2858 (2014/05/06)
An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent. This journal is the Partner Organisations 2014.