Effect of noncovalent interactions in ion pairs on hypervalent iodines: inversion of regioselectivity in sulfonyloxylactonization?
Organic Chemistry Frontiers Pub Date: 2021-04-28 DOI: 10.1039/D1QO00523E
Abstract
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.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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