Hypervalent iodine-mediated formation of S-S, C-S, C-O, and C-N bonds

被引：3

作者：

Kuo, Yu-Tsen ^{[1
]}

Chai, Te-Jung ^{[1
]}

Lin, Cheng-Kun ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung, Taiwan

来源：

SYNTHETIC COMMUNICATIONS | 2023年 / 53卷 / 11期

关键词：

Acylation; acyloxyphosphonium; amide; disulfide; hypervalent iodine reagent; thioester; REACTIVITY; ACTIVATION; CHEMISTRY; MECHANISM;

D O I：

10.1080/00397911.2023.2197119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Di(4-nitrobenzoyloxy)iodo]benzene (1), a hypervalent iodine compound, is easy to prepare and stable as a solid, and was shown to be a useful functional group transforming agent in this report. Oxidative synthesis of symmetrical disulfides from thiols in the presence of compound 1 alone was performed in 58-100% yields. Furthermore, ESI-MS demonstrated that premixing of 1 and Ph3P yields the corresponding acyloxyphosphonium, which can acylate thiols to produce thioesters in 69-100% yields. With the assistance of a mixture of 1 and Ph3P, hydroxy and amino groups were benzoylated to esters and amides, respectively, also in 9-100% yields.

引用

页码：795 / 807

页数：13

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