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

Abstract

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.

Graphical Abstract

Keywords:

• Acylation
• acyloxyphosphonium
• amide
• disulfide
• hypervalent iodine reagent
• thioester

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the National Chung Hsing University. We thank the Instrument Center at National Chung Hsing University (NCHU) for providing valuable assistance on LC-MS/MS [MOST 110-2731-M-005-001] and the access of ESI mass spectrum of the intermediate ii by Prof. I-Chung Lu of the Department of Chemistry at the National Chung Hsing University. This work was supported by the Ministry of Science and Technology of Taiwan [grant no. MOST 111-2113-M-005-019-] and the National Chung Hsing University.