2026-03-06T12:27:47Z https://nagoya.repo.nii.ac.jp/oai

oai:nagoya.repo.nii.ac.jp:00030542 2023-01-16T04:24:08Z 320:321:322

Halogen-Bonding Interaction between I2 and N-Iodosuccinimide in Lewis Base-Catalyzed Iodolactonization Horibe, Takahiro Tsuji, Yasutaka Ishihara, Kazuaki open access “This document is the Accepted Manuscript version of a Published Work that appeared in final form in [Organic Letters], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-3IRZKRT9IWGWNK2ERFHP].” Iodine Reagents Halogen bonding Lewis bases Cations The halogen-bonding interaction between I2 and N-iodosuccinimide (NIS) stabilized by a Lewis base (LB) has been explored. 1H NMR, nuclear Overhauser effect (NOE), and diffusion-ordered NMR spectroscopy (DOSY) suggest the generation of a 1:1:1 assembly, LB–I2–NIS. In contrast, when N-iodotrifluoromethanesulfonimide (INTf2) is used instead of NIS, LB–I5^+–LB is generated. On the basis of these results in combination with density functional theory (DFT) calculations, we propose a mechanism for the formation of I2–NIS and the subsequent generation of an active iodinating species LB–I^+. ファイル公開：2021-06-19 ACS Publications 2020-06-19 eng journal article AM http://hdl.handle.net/2237/00032727 https://nagoya.repo.nii.ac.jp/records/30542 https://doi.org/10.1021/acs.orglett.0c01735 1523-7060 Organic Letters 22 12 4888 4892 https://nagoya.repo.nii.ac.jp/record/30542/files/2nd_revised_manuscript.pdf application/pdf 1.5 MB 2021-06-19