Simple and Efficient Halotosyloxylation Reaction of Alkynes Using Poly{[4-(hydroxy)(tosyloxy)iodo]styrene}
Jiang-Min Chen, Xian Huang*
*Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028,
P. R. China, Email: huangx
mail.hz.zj.cn
J.-M. Chen, X. Huang, Synthesis, 2004, 1557-1558.
DOI: 10.1055/s-2004-822373
Abstract
Poly{[4-(hydroxy)(tosyloxy)iodo]styrene} was efficient in the halotosyloxylation reaction of alkynes with iodine or NBS or NCS. The polymer reagent could be regenerated and reused.
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Details
The document discusses a study on the halotosyloxylation reaction of alkynes using poly{[4-(hydroxy)(tosyloxy)iodo]styrene}. This polymer-supported reagent is efficient in reactions with iodine, N-bromosuccinimide (NBS), or N-chlorosuccinimide (NCS) to produce multifunctional olefins. The key advantage of this method is the ability to regenerate and reuse the polymer reagent, making it environmentally friendly. The reactions were conducted in anhydrous CH2Cl2 at room temperature, yielding (E)-β-iodo-α-(p-toluenesulfonyloxy)alkenes in good yields. The study highlights the mild reaction conditions, ease of manipulation, and good yields. The polymer reagent's regeneration was confirmed by its consistent reactivity in subsequent reactions. The document includes detailed experimental procedures, compound characterizations, and yields for various substrates. The research was supported by the National Natural Science Foundation of China.
Key Words
Poly{[4-(hydroxy)(tosyloxy)iodo]styrene}, Koser's Reagent, Halotosyloxylation Reaction, Alkynes, Enols, Vinyliodides, α-Iodoketones, Vinylbromides, α-Bromoketones, Vinylchlorides, α-Chloroketones, Hypervalent Iodine Compounds
ID: J66-Y2004-2140
