Halogen-Bonding Interaction between I2 and N-lodosuccinimide in Lewis Base-Catalyzed lodolactonization

被引：7

作者：

Horibe, Takahiro ^{[1
]}

Tsuji, Yasutaka ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; CRYSTAL-STRUCTURE; IODOLACTONIZATION; BROMOLACTONIZATION; BROMOCYCLIZATION; IODINE;

D O I：

10.1021/acs.orglett.0c01735

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The halogen-bonding interaction between I-2 and N-iodosuccinimide (NIS) stabilized by a Lewis base (LB) has been explored. H-1 NMR, nuclear Overhauser effect (NOE), and diffusion-ordered NMR spectroscopy (DOSY) suggest the generation of a 1 : 1 : 1 assembly, LB-I-2-NIS. In contrast, when N-iodotrifluoromethanesulfonimide (INTf2) is used instead of NIS, LB-I-5(+)-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 I-2-NIS and the subsequent generation of an active iodinating species LB-I+.

引用

页码：4888 / 4892

页数：5

共 13 条

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