Introduction of N,N'-disulfonylhydrazines as new sulfonylating reagents for highly efficient synthesis of (E)-β-iodovinyl arenesulfones under mild conditions
Introduction of N,N'-disulfonylhydrazines as new sulfonylating reagents for highly efficient synthesis of (E)-β-iodovinyl arenesulfones under mild conditions
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DOI：
10.1016/j.cclet.2019.12.040
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发表时间：
2020-01
影响因子：
9.1
通讯作者：
Dong‐Fen Luo;L. Min;Weiping Zheng;L. Shan;Xinyan Wang-;Yuefei Hu
中科院分区：
文献类型：
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作者：
Dong‐Fen Luo;L. Min;Weiping Zheng;L. Shan;Xinyan Wang-;Yuefei Hu
早在世纪以前，N，N ′-二磺酰肼就已被证明是磺酰基取代肼类化合物中反应活性最高的磺酰基自由基前体。然而，这些化合物产生的磺酰基自由基除了在“溶剂笼效应”控制下的简单的二砜自二聚合成外，还没有用于有机合成。本文介绍了N，N′-二磺酰肼类新磺酰化试剂及其与NIS的组合物作为炔的碘磺酰化试剂。最后，通过在THF水溶液中室温下将炔、α-N，N′-二磺酰肼和NIS混合反应5 min，得到了一种高效合成（E）-β-碘代乙烯基芳砜的方法。
N,N'-Disulfonylhydrazines have been proven to be the most reactive precursors of the sulfonyl radicals among all types of sulfonyl substituted hydrazines as early as half a century ago. However, the sulfonyl radicals generated from these compounds have not been used in organic synthesis except the simple self-dimerization synthesis of disulfones controlled by the “solvent-cage-effects”. In this article,N,N′-disulfonylhydrazines were introduced as new sulfonylating reagents and their combinations with NIS were disclosed as new iodosulfonylating reagents of alkynes. Finally, a highly efficient method for the synthesis of (E)-β-iodovinyl arenesulfones was developed by mixing an alkyne, aN,N′-disulfonyl-hydrazine and NIS in aqueous THF at room temperature for 5 min.