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Article ; Online: Organophosphates as Versatile Substrates in Organic Synthesis.

Oeser, Petr / Tobrman, Tomáš

2024 Volume 29, Issue 7

Abstract: This review summarizes the applications of organophosphates in organic synthesis. After a brief introduction, it discusses cross-coupling reactions, including both transition-metal-catalyzed and transition-metal-free substitution reactions. Subsequently, ...

Abstract	This review summarizes the applications of organophosphates in organic synthesis. After a brief introduction, it discusses cross-coupling reactions, including both transition-metal-catalyzed and transition-metal-free substitution reactions. Subsequently, oxidation and reduction reactions are described. In addition, this review highlights the applications of organophosphates in the synthesis of natural compounds, demonstrating their versatility and importance in modern synthetic chemistry.
Language	English
Publishing date	2024-04-02
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules29071593
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Article ; Online: Room-Temperature Negishi Reaction of Trisubstituted Vinyl Phosphates for the Synthesis of Tetrasubstituted Alkenes.

Čubiňák, Marek / Tobrman, Tomáš

The Journal of organic chemistry

2020 Volume 85, Issue 16, Page(s) 10728–10739

Abstract: The present study investigated the ability of bromovinyl phosphates to react with organozinc reagents at room temperature during palladium-catalyzed reactions. It was determined that both the bromine atom and the phosphate group were successfully ... ...

Abstract	The present study investigated the ability of bromovinyl phosphates to react with organozinc reagents at room temperature during palladium-catalyzed reactions. It was determined that both the bromine atom and the phosphate group were successfully substituted by means of the reaction with the organozinc reagents, thereby allowing for the synthesis of cyclic and acyclic tetrasubstituted double bonds. The low stability of the organozinc compounds in an acidic environment was exploited to accomplish the synthesis of alkenes using a one-pot, two-step experimental setup.
Language	English
Publishing date	2020-08-03
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c01254
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Article: Room-Temperature Negishi Reaction of Trisubstituted Vinyl Phosphates for the Synthesis of Tetrasubstituted Alkenes

Čubiňák, Marek / Tobrman, Tomáš

Journal of organic chemistry. 2020 July 17, v. 85, no. 16

2020

Abstract	The present study investigated the ability of bromovinyl phosphates to react with organozinc reagents at room temperature during palladium-catalyzed reactions. It was determined that both the bromine atom and the phosphate group were successfully substituted by means of the reaction with the organozinc reagents, thereby allowing for the synthesis of cyclic and acyclic tetrasubstituted double bonds. The low stability of the organozinc compounds in an acidic environment was exploited to accomplish the synthesis of alkenes using a one-pot, two-step experimental setup.
Keywords	alkenes ; ambient temperature ; bromine ; organic chemistry ; phosphates
Language	English
Dates of publication	2020-0717
Size	p. 10728-10739.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c01254
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Article ; Online: Recent Progress Concerning the

Oeser, Petr / Koudelka, Jakub / Petrenko, Artem / Tobrman, Tomáš

Molecules (Basel, Switzerland)

2021 Volume 26, Issue 16

Abstract: This review summarizes the current state-of-the-art procedures in terms of the preparation ... ...

Abstract	This review summarizes the current state-of-the-art procedures in terms of the preparation of
Language	English
Publishing date	2021-08-22
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules26165079
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Article ; Online: Substrate-Controlled Regioselective Bromination of 1,2-Disubstituted Cyclobutenes: An Application in the Synthesis of 2,3-Disubstituted Cyclobutenones.

Edlová, Tereza / Dvořáková, Hana / Eigner, Václav / Tobrman, Tomáš

The Journal of organic chemistry

2021 Volume 86, Issue 8, Page(s) 5820–5831

Abstract: Easily available disubstituted cyclobutenes were regioselectively halogenated at the allylic position by means of a reaction with bromine. The regioselectivity of bromination is controlled by the presence of a carbocation-stabilizing group. The prepared ... ...

Abstract	Easily available disubstituted cyclobutenes were regioselectively halogenated at the allylic position by means of a reaction with bromine. The regioselectivity of bromination is controlled by the presence of a carbocation-stabilizing group. The prepared disubstituted 3-bromocyclobutenes were converted into the corresponding disubstituted cyclobutenones. On the basis of the performed experiments, the mechanism behind the bromination reaction was also proposed.
Language	English
Publishing date	2021-04-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.1c00261
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Article: Substrate-Controlled Regioselective Bromination of 1,2-Disubstituted Cyclobutenes: An Application in the Synthesis of 2,3-Disubstituted Cyclobutenones

Edlová, Tereza / Dvořáková, Hana / Eigner, Václav / Tobrman, Tomáš

Journal of organic chemistry. 2021 Apr. 05, v. 86, no. 8

2021

Abstract	Easily available disubstituted cyclobutenes were regioselectively halogenated at the allylic position by means of a reaction with bromine. The regioselectivity of bromination is controlled by the presence of a carbocation-stabilizing group. The prepared disubstituted 3-bromocyclobutenes were converted into the corresponding disubstituted cyclobutenones. On the basis of the performed experiments, the mechanism behind the bromination reaction was also proposed.
Keywords	bromination ; bromine ; organic chemistry ; regioselectivity
Language	English
Dates of publication	2021-0405
Size	p. 5820-5831.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.1c00261
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Substituted polythiophene-based sensor for detection of ammonia in gaseous and aqueous environment

Shishkanova, Tatiana V. / Tobrman, Tomáš / Otta, Jaroslav / Broncová, Gabriela / Fitl, Přemysl / Vrňata, Martin

J Mater Sci. 2022 Oct., v. 57, no. 37 p.17870-17882

2022

Abstract: This manuscript presents the preparation of polymer layers based on polythiophene (PTh) and its 3-substituted derivatives (substituents 4-(CH₃O)C₆H₄ and 4-(CF₃)C₆H₄ marked as PThOCH₃ and PThCF₃, respectively) on platinum electrodes by cyclic voltammetry ( ...

Abstract	This manuscript presents the preparation of polymer layers based on polythiophene (PTh) and its 3-substituted derivatives (substituents 4-(CH₃O)C₆H₄ and 4-(CF₃)C₆H₄ marked as PThOCH₃ and PThCF₃, respectively) on platinum electrodes by cyclic voltammetry (CV). The polymerization process and the morphology of resulting layers were discussed analysing of CV-voltammograms and scanning electron microscopy (SEM), respectively. Subsequently, the prepared polymers were tested as active/sensitive media of two types of sensors: (i) electrochemical sensor detecting ammonia in aqueous environment, whose response was evaluated by electrochemical impedance spectroscopy (EIS); (ii) chemiresistor detecting NH₃ in atmosphere, whose response was evaluated by measurement of resistance. It was found that both the physical (morphology, homogeneity, relative thickness) and receptor properties of the polymer layer deposited on electrode surface are significantly affected by the nature of substituent attached to the thiophene ring. The mutual context of ammonia detection in both environments is discussed.
Keywords	ammonia ; dielectric spectroscopy ; electrodes ; electron microscopy ; platinum ; polymerization ; polymers ; sensors (equipment) ; thiophene ; voltammetry
Language	English
Dates of publication	2022-10
Size	p. 17870-17882.
Publishing place	Springer US
Document type	Article ; Online
ZDB-ID	2015305-3
ISSN	1573-4803 ; 0022-2461
ISSN (online)	1573-4803
ISSN	0022-2461
DOI	10.1007/s10853-022-07694-8
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Article ; Online: Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones

Oeser, Petr / Koudelka, Jakub / Dvořáková, Hana / Tobrman, Tomáš

RSC advances

2020 Volume 10, Issue 58, Page(s) 35109–35120

Abstract: We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3- ...

Abstract	We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3-dienes
Language	English
Publishing date	2020-09-22
Publishing country	England
Document type	Journal Article
ISSN	2046-2069
ISSN (online)	2046-2069
DOI	10.1039/d0ra07472a
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Article ; Online: Formal Transition-Metal-Catalyzed Phosphole C-H Activation for the Synthesis of Pentasubstituted Phospholes.

Polák, Peter / Čejka, Jan / Tobrman, Tomáš

Organic letters

2020 Volume 22, Issue 6, Page(s) 2187–2190

Abstract: Unprecedented formal transition-metal-catalyzed phosphole C-H functionalization is described in this paper. Pentasubstituted phospholes were prepared via the copper-catalyzed reaction of 1,3,4-trisubstituted phosphole with aryl iodides or bromides under ... ...

Abstract	Unprecedented formal transition-metal-catalyzed phosphole C-H functionalization is described in this paper. Pentasubstituted phospholes were prepared via the copper-catalyzed reaction of 1,3,4-trisubstituted phosphole with aryl iodides or bromides under distinct conditions. The developed methodology is able to accommodate a wide variety of substituents, including aryl, heteroaryl, and alkenyl.
Language	English
Publishing date	2020-03-03
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.0c00359
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Article: Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents

Oeser, Petr / Koudelka, Jakub / Dvořáková, Hana / Tobrman, Tomáš

RSC advances. 2020 Sept. 22, v. 10, no. 58

2020

Abstract	We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3-dienes via the reaction with aryllithium reagents. Moreover, the vinyl phosphordiamidates were converted into α,β-unsaturated ketones using Grignard reagents. Based on the performed experiments, we proposed a reaction mechanism, which was confirmed by means of the isolation of key intermediates.
Keywords	Grignard reagents ; esters ; ketones ; phosphates ; reaction mechanisms
Language	English
Dates of publication	2020-0922
Size	p. 35109-35120.
Publishing place	The Royal Society of Chemistry
Document type	Article
ISSN	2046-2069
DOI	10.1039/d0ra07472a
Database	NAL-Catalogue (AGRICOLA)

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