氟苯并二氧杂环戊烯-BF 试剂在醚溶剂中碘化（III）炔烃醚化。
Fluorobenziodoxole-BF Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent.
机构信息
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, P.R. China.
出版信息
Chem Asian J. 2020 Jul 16;15(14):2166-2169. doi: 10.1002/asia.202000653. Epub 2020 Jun 24.
A combination of fluorobenziodoxole (FBX) and BF ⋅ OEt in cyclopentyl methyl ether promotes regio- and stereoselective addition of benziodoxole and methoxy groups to alkynes. This difunctionalization reaction tolerates a variety of functionalized internal and terminal alkynes to afford trans-β-alkoxyvinylbenziodoxoles, which represent versatile precursors to stereochemically well-defined multisubstituted vinyl ethers. The reaction is proposed to involve cleavage of the I-F bond of FBX by BF , followed by electrophilic activation of the alkyne by the resulting cationic I species that triggers the nucleophilic addition of the ethereal oxygen.
氟苯并[ d ]噁唑（FBX）与 BF ⋅ ⋅ OEt 的组合在环戊基甲醚中促进苯并[ d ]噁唑和甲氧基基团对炔烃的区域和立体选择性加成。这种双官能团化反应可耐受多种官能化的内部和末端炔烃，得到反式-β-烷氧基乙烯基苯并噁唑，它们是立体化学定义明确的多取代乙烯基醚的多功能前体。该反应被认为涉及 FBX 的 I-F 键被 BF ⋅ ⋅ OEt 裂解，随后由生成的阳离子 I 物种对炔烃进行亲电活化，引发亲核加成醚氧。
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