Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and Their Application to Electrophilic Pentafluorosulfanylarylation of C-, O-, N-, and S-Nucleophiles

Kohei Matsuzaki; Kenta Okuyama; Etsuko Tokunaga; Norimichi Saito; Motoo Shiro; Norio Shibata

doi:10.1021/acs.orglett.5b01323

Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and Their Application to Electrophilic Pentafluorosulfanylarylation of C-, O-, N-, and S-Nucleophiles

Org Lett. 2015 Jun 19;17(12):3038-41. doi: 10.1021/acs.orglett.5b01323. Epub 2015 May 29.

Authors

Kohei Matsuzaki¹, Kenta Okuyama¹, Etsuko Tokunaga¹, Norimichi Saito², Motoo Shiro³, Norio Shibata¹

Affiliations

¹ †Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
² ‡Pharmaceutical Division, Ube Industries, Ltd., Seavans North Building 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan.
³ §Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666, Japan.

PMID: 26023887
DOI: 10.1021/acs.orglett.5b01323

Abstract

Novel reagents for the electrophilic introduction of pentafluorosulfanyl (SF5) arenes into target molecules are disclosed. Unsymmetrical diaryliodonium salts 1 having SF5-arenes were synthesized by a one-pot process from iodo-SF5-benzenes 2 in good yields. The SF5-aryliodonium salts 1 were found to be efficient for the electrophilic SF5-arylation of carbon and heterocentered nucleophiles to furnish the corresponding substituted SF5-arenes in good to high yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Indicators and Reagents / chemistry*
Iodine / chemistry*
Molecular Structure
Onium Compounds / chemical synthesis*
Onium Compounds / chemistry
Salts / chemistry*

Substances

Hydrocarbons, Fluorinated
Indicators and Reagents
Onium Compounds
Salts
Iodine