Chinese Journal of Organic Chemistry >
Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes
Received date: 2017-11-30
Revised date: 2018-01-08
Online published: 2018-01-26
Supported by
Project supported by the National Natural Science Foundation of China (No. 21502076), the Hundred-Talent Program of Hefei City and the Outstanding Young Talents Scheme of Jiangxi Province (No. 20171BCB23039).
Iodoalkynes and diiodoalkenes are valuable intermediates used extensively for C—C, C—O and C—N bonds formation. Therefore, the development of new method for the synthesis of these compunds is desirable. In this work, a novel and switchable protocol for the synthesis of iodoalkynes and diiodoalkenes has been developed, which were formed from terminal alkynes using the same reagent system of ZnI2 and tert-butyl nitrite in the presence or absence of triethylamine, respectively. The iodoalkyne formation is operationally simple, mild (weak base and room temperature), and tolerant of a large range of functional groups. In contrast, the diiodoalkene transformation shows interesting dependence on the electron property, and only electron-rich and neutral compounds are viable substrates. The control experiments performed suggest that iodoalkynes and diiodoalkenes are not interchangeable under a series of reaction conditions, including the optimized conditions, which can be explained by the mechanism in which both of the reactions involve a iodonium intermediate formed directly from a terminal alkyne.
Key words： iodoalkyne; diiodoalkene; tert-butyl nitrite; alkyne; zinc iodide
Chen Suo , Zhang Xiaowei , Zhao Hui , Guo Xiaohong , Hu Xiangguo . Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1172 -1176 . DOI: 10.6023/cjoc201711050
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