Internal Delivery of Soft Chlorine and Bromine Atoms: Stereoselective Synthesis of (E)-β-Halogenovinyl(aryl)-λ3-iodanes through Domino λ3-Iodanation−1,4-Halogen Shift−Fluorination of Alkynes
Internal Delivery of Soft Chlorine and Bromine Atoms: Stereoselective Synthesis of (E)-β-Halogenovinyl(aryl)-λ3-iodanes through Domino λ3-Iodanation−1,4-Halogen Shift−Fluorination of Alkynes
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DOI：
10.1021/ol071345q
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发表时间：
2007-07
期刊：
影响因子：
5.2
通讯作者：
M. Ochiai;Masaya Hirobe;A. Yoshimura;Yoshio Nishi;and Kazunori Miyamoto;M. Shiro
中科院分区：
文献类型：
--
作者：
M. Ochiai;Masaya Hirobe;A. Yoshimura;Yoshio Nishi;and Kazunori Miyamoto;M. Shiro
4-（二氟碘）甲苯诱导的多米诺λ3-碘化− 1，4-卤素移位−扩环− 5-卤代戊炔与四元、五元或六元碳环的反应立体选择性地高产率地得到扩环的（E）-δ-氟-β-卤代乙烯基-λ3-碘烷，可能是通过五元卤离子的中间作用。使用内炔使得合成具有确定立体化学的四取代β-卤代乙烯基-λ3-碘烷成为可能。
4-(Difluoroiodo)toluene-induced domino λ3-iodanation−1,4-halogen shift−ring enlargement−fluorination reaction of 5-halopentynes with a four-, five-, or six-membered carbocycle afforded the ring-expanded (E)-δ-fluoro-β-halovinyl-λ3-iodanes stereoselectively in high yields, probably via the intermediacy of five-membered halonium ions. Use of internal alkynes makes it possible to synthesize tetrasubstituted β-halovinyl-λ3-iodanes with defined stereochemistry.