Metal-Free Synthesis of β-Bromoalkenyl Sulfides via Deoxygenative Bromination/Olefination/Sulfenylation of Ketones with SulfonylHydrazides and Pyridinium Tribromide

作     者：Yishu Bao Lingyu Zhong Qiaodan Hou Qingfa Zhou Fulai Yang 

作者机构：State Key Laboratory of Natural Medicines Department of Organic Chem- istry China Pharmaceutical University Nanjing Jiangsu 210009 China 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2018年第36卷第11期

页      面：1063-1068页

核心收录：

学科分类：07[理学] 

基　　金：This work was financially supported by the National Natural Science Foundation of China (Nos. 21502182  21102179 and 21572271)  Qing Lan Project of Jiangsu Province  National Found for Fostering Talents of Basic Science (J1030830)  the Fundamen- tal Research Funds for the Central Universities (No. 3010050077) and Postgraduate Scientific Research Innovation Projects of Jiangsu Province (No. KYCX17_0664) 

主　　题：ketones sulfonyl hydrazides deoxygenative β‐bromoalkenyl sulfides pyridinium tribromide 

摘      要：A novel metal‐free method for synthesis of β‐bromoalkenyl sulfides via deoxygenative bromination/olefination/sulfenylation process using commercially available ketones, sulfonyl hydrazides and pyridinium tribromide as starting materials has been developed. In this reaction, pyridinium tribromide plays the role of oxidant and substrate, wherein water and molecular nitrogen are generated as environmentally benign by‐products. Preliminary investigation revealed that vinyl bromides were critical intermediate. Importantly, this protocol not only obviates the use of alkynes and traditional sulfenylating agents, but also reveals that ketones can be used as precursors of vinyl bromides.