Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride

KONHEFR, Martin, Lenka MICHALCOVÁ, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL, Ctibor MAZAL and Karel LACINA. Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride. Tetrahedron Letters. Oxford: Pergamon-Elsevier Science Ltd, 2020, vol. 61, No 9, p. 1-4. ISSN 0040-4039. Available from: https://dx.doi.org/10.1016/j.tetlet.2019.151535.

Basic information

Original name

Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride

Name in Czech

Neočekávaná reaktivita ferrocenyl-iminoboronátů: štěpení ortho-iminových vazeb oxidací v přítomnosti nevodného chloridu sodného

Authors

KONHEFR, Martin (203 Czech Republic, belonging to the institution), Lenka MICHALCOVÁ (203 Czech Republic, belonging to the institution), Monika SKRUTKOVÁ LANGMAJEROVÁ (203 Czech Republic, belonging to the institution), Zdeněk GLATZ (203 Czech Republic, belonging to the institution), Petr SKLÁDAL (203 Czech Republic, belonging to the institution), Ctibor MAZAL (203 Czech Republic, belonging to the institution) and Karel LACINA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Tetrahedron Letters, Oxford, Pergamon-Elsevier Science Ltd, 2020, 0040-4039

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Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.415

RIV identification code

RIV/00216224:14310/20:00114051

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.tetlet.2019.151535

UT WoS

000517855700011

Keywords (in Czech)

Ferocen; Boronová kyselina; Elektrochemicky usnadněná interakce; Komplexace alkalických kovů; Iminová vazba

Keywords in English

Ferrocene; Boronic acid; Electrochemically facilitated interaction; Alkali metal complexation; Imine bond

Tags

rivok

Tags

International impact, Reviewed

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Abstract

V originále

The boronic acid moiety in the proximity of electron-donating structures in ((ferrocenylimino)methyl)phenylboronic acid 1 significantly improves the reactivity of the molecule. The ortho regioisomer 1a exhibits a two-fold higher affinity to NaCl compared to its meta 1b and para 1c isomers, respectively. Moreover, the double imine bond in 1a was broken by the interaction with NaCl in methanol upon activation by electrochemical oxidation.

In Czech

Boronová kyselina v blízkosti elektron-donorních struktur ve ((ferocenylimino)methyl)fenylboronové kyselině 1 signifikantně zlepšuje reaktivitu této molekuly. Ortho isomer 1a vykazuje vyšší afinitu k NaCl ve srovnání s meta 1b a para 1c isomery. Dvojná iminová vazba v 1a byla navíc rozštěpena interakcí 1a s NaCl v methanolu při aktivaci 1a elektrochemickou oxidací.

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Links

GJ19-16273Y, research and development project	Name: ROS-indukované uvolňování léčiv založené na interakcích ferocenylboronátů Investor: Czech Science Foundation, ROS-Induced Drug Release Based on Interactions of Ferrocenylboronates
LQ1601, research and development project	Name: CEITEC 2020 (Acronym: CEITEC2020) Investor: Ministry of Education, Youth and Sports of the CR
MUNI/A/1252/2019, interní kód MU	Name: Podpora biochemického výzkumu v roce 2020 Investor: Masaryk University, Category A