Stereoselective hydrozirconation of alkynylsulfide and regioselective synthesis of haloalkenyl sulfide via electrophile-switched halogenation of thioalkenyl zirconocene

作者：Zheng, Weixin^*; Hong, Ya; Wang, Ping; Zheng, Fenfen; Zhang, Yanjing; Wang, Wei

来源：Tetrahedron Letters, 2013, 54(28): 3643-3646.

DOI：10.1016/j.tetlet.2013.04.122

• Alkynyl sulfide
• Hydrozirconation
• Syn-addition
• Electrophile-switched halogenation
• Stereo- and regioselectivity

Stereoselective preparation of alkenyl sulfide was carried out via syn-hydrozirconation of the alkynyl sulfide. Regiochemistry of halogenation of the thioalkenyl zirconocene could be switched by different halides. alpha-Chloroalkenyl sulfide or beta-haloalkenyl sulfide (Br, I) could be obtained by the treatment of NCS or NBS (NIS), respectively. Possible mechanism of halogenation of the thioalkenyl zirconocene was set up herein.

• 出版日期2013-7-10
• 单位杭州师范大学