Effect of noncovalent interactions in ion pairs on hypervalent iodines: inversion of regioselectivity in sulfonyloxylactonization
Effect of noncovalent interactions in ion pairs on hypervalent iodines: inversion of regioselectivity in sulfonyloxylactonization
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DOI：
10.1039/d1qo00523e
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发表时间：
2021-04
影响因子：
5.4
通讯作者：
Yoshihiro Nishimoto;Masaki Fujie;Junki Hara;M. Yasuda
中科院分区：
文献类型：
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作者：
Yoshihiro Nishimoto;Masaki Fujie;Junki Hara;M. Yasuda
我们合成了新的高价碘具有阳离子杂环部分附近的碘（III）中心。在2-乙烯基苯甲酸的磺酰氧基内酰化反应中，新型高价碘化合物表现出与普通PhI（OAc）2完全不同的区域选择性。磺酰氧基基团和阳离子杂环部分之间的非共价相互作用导致了区域选择性的显着变化，这是通过观察中间体和密度泛函理论研究，包括非共价相互作用分析。
We synthesized novel hypervalent iodines possessing cationic heterocyclic moieties nearby the iodine(III) center. The novel hypervalent iodines exhibited a totally different regioselectivity from common PhI(OAc)2 during the sulfonyloxylactonization of 2-vinylbenzoic acids. The noncovalent interactions between the sulfonyloxy groups and the cationic heterocyclic moieties resulted in a significant change in the regioselectivity, which was revealed by the observation of intermediates and density functional theory studies including noncovalent interaction analysis.