Synthesis of pyridine trans-tetrafluoro-λ6-sulfane derivatives via radical addition

Prajwalita Das; Masahiro Takada; Etsuko Tokunaga; Norimichi Saito; Norio Shibata

doi:10.1039/C7QO00994A

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Synthesis of pyridine trans-tetrafluoro-λ⁶-sulfane derivatives via radical addition†

Prajwalita Das,^a Masahiro Takada,^a Etsuko Tokunaga,

^a Norimichi Saito^b and Norio Shibata

*^a

Author affiliations

* Corresponding authors

^a Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp

^b Pharmaceutical Division, Ube Industries, Ltd., Seavans North Bldg., 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan

Abstract

Pyridine tetrafluoro-λ⁶-sulfanes (SF₄) with alkenyl or alkyl substituents have been synthesized for the first time via the radical addition reactions of pyridine-SF₄ chlorides to alkynes or alkenes in good to high yields. X-Ray crystallographic analysis and DFT calculations disclosed an octahedral symmetrical trans-configuration of the hypervalent tetrafluorosulfanyl center. In contrast to phenyl-SF₄ analogues, pyridine-SF₄ compounds were found to be stable, which expands the utility of pyridine-SF₄ compounds.

This article is part of the themed collections: Organic Chemistry Frontiers HOT articles for 2018 and Organic Chemistry Frontiers HOT articles for 2017

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Article information

DOI: https://doi.org/10.1039/C7QO00994A
Article type: Research Article
Submitted: 01 Nov 2017
Accepted: 16 Nov 2017
First published: 16 Nov 2017

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Org. Chem. Front., 2018,5, 719-724

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Synthesis of pyridine trans-tetrafluoro-λ⁶-sulfane derivatives via radical addition

P. Das, M. Takada, E. Tokunaga, N. Saito and N. Shibata, Org. Chem. Front., 2018, 5, 719 DOI: 10.1039/C7QO00994A

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