Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives

Akira Yoshimura; Christopher D. Huss; Mackenzie Liebl; Gregory T. Rohde; Scott M. Larson; Gunnar B. Frahm; Mattew W. Luedtke; Tanner J. Schumacher; Zachary S. Gardner; Viktor V. Zhdankin; Pavel S. Postnikov; Mekhman S. Yusubov; Tsugio Kitamura; Akio Saito

doi:10.1002/adsc.202100341

Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives

Akira Yoshimura, Christopher D. Huss, Mackenzie Liebl, Gregory T. Rohde, Scott M. Larson, Gunnar B. Frahm, Mattew W. Luedtke, Tanner J. Schumacher, Zachary S. Gardner, Viktor V. Zhdankin, Pavel S. Postnikov, Mekhman S. Yusubov, Tsugio Kitamura, Akio Saito

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8 Scopus citations

Abstract

Pseudocyclic β-trifluorosulfonyloxy vinylbenziodoxolones were prepared starting from hydroxybenziodoxolones and alkynes in the presence of trifluoromethanesulfonic acid. The reaction of these compounds with azide anion leads to β-azido vinylbenziodoxolones as products of vinylic nucleophilic substitution in which addition-elimination reactions occur and the double bond configuration is retained. The structures of β-trifluorosulfonyloxy vinylbenziodoxolone and β-azido vinylbenziodoxolone were established by single crystal X-ray diffraction. (Figure presented.).

Original language	English (US)
Pages (from-to)	3365-3371
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	13
DOIs	https://doi.org/10.1002/adsc.202100341
State	Published - Jul 1 2021

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-21-73-20031) and National Science Foundation (CHE-1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). T. K is thankful to JSPS KAKENHI Grant Number 19K05423.

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF‐21‐73‐20031) and National Science Foundation (CHE‐1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). T. K is thankful to JSPS KAKENHI Grant Number 19K05423.

Publisher Copyright:
© 2021 Wiley-VCH GmbH

Keywords

Micheal acceptor
alkenyliodonium
hypervalent iodine
pseudocyclic
vinylbenziodoxolones

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Yoshimura, A., Huss, C. D., Liebl, M., Rohde, G. T., Larson, S. M., Frahm, G. B., Luedtke, M. W., Schumacher, T. J., Gardner, Z. S., Zhdankin, V. V., Postnikov, P. S., Yusubov, M. S., Kitamura, T., & Saito, A. (2021). Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives. Advanced Synthesis and Catalysis, 363(13), 3365-3371. https://doi.org/10.1002/adsc.202100341

Yoshimura, A, Huss, CD, Liebl, M, Rohde, GT, Larson, SM, Frahm, GB, Luedtke, MW, Schumacher, TJ, Gardner, ZS, Zhdankin, VV, Postnikov, PS, Yusubov, MS, Kitamura, T & Saito, A 2021, 'Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives', Advanced Synthesis and Catalysis, vol. 363, no. 13, pp. 3365-3371. https://doi.org/10.1002/adsc.202100341

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N2 - Pseudocyclic β-trifluorosulfonyloxy vinylbenziodoxolones were prepared starting from hydroxybenziodoxolones and alkynes in the presence of trifluoromethanesulfonic acid. The reaction of these compounds with azide anion leads to β-azido vinylbenziodoxolones as products of vinylic nucleophilic substitution in which addition-elimination reactions occur and the double bond configuration is retained. The structures of β-trifluorosulfonyloxy vinylbenziodoxolone and β-azido vinylbenziodoxolone were established by single crystal X-ray diffraction. (Figure presented.).

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Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives

Abstract

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Keywords

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