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The present paper examines both catalyst-free and KF-mediated hydroboration of carbonyl compounds with the use of quantum-chemical methods.
Mateusz Nowicki; Krzysztof Kuciński; Grzegorz Hreczycho; Marcin Hoffmann. Catalytic and non-catalytic hydroboration of carbonyls: quantum-chemical studies. Organic & Biomolecular Chemistry 2021, 19, 3004 -3015.
AMA StyleMateusz Nowicki, Krzysztof Kuciński, Grzegorz Hreczycho, Marcin Hoffmann. Catalytic and non-catalytic hydroboration of carbonyls: quantum-chemical studies. Organic & Biomolecular Chemistry. 2021; 19 (13):3004-3015.
Chicago/Turabian StyleMateusz Nowicki; Krzysztof Kuciński; Grzegorz Hreczycho; Marcin Hoffmann. 2021. "Catalytic and non-catalytic hydroboration of carbonyls: quantum-chemical studies." Organic & Biomolecular Chemistry 19, no. 13: 3004-3015.
Apart from some specific synthetic solutions, a dehydrogenative coupling of silanols with hydrosilanes seems to be the most atom-economical and practical method for the formation of unsymmetrical siloxanes.
Krzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. Silylation of silanols with hydrosilanes via main-group catalysis: the synthesis of unsymmetrical siloxanes and hydrosiloxanes. Inorganic Chemistry Frontiers 2020, 7, 4190 -4196.
AMA StyleKrzysztof Kuciński, Hanna Stachowiak, Grzegorz Hreczycho. Silylation of silanols with hydrosilanes via main-group catalysis: the synthesis of unsymmetrical siloxanes and hydrosiloxanes. Inorganic Chemistry Frontiers. 2020; 7 (21):4190-4196.
Chicago/Turabian StyleKrzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. 2020. "Silylation of silanols with hydrosilanes via main-group catalysis: the synthesis of unsymmetrical siloxanes and hydrosiloxanes." Inorganic Chemistry Frontiers 7, no. 21: 4190-4196.
Hydroelementation enables a facile reduction or functionalization of several unsaturated systems, and thus activation of such bonds like B–H and Si–H is a powerful synthetic tool.
Krzysztof Kuciński; Grzegorz Hreczycho. Hydrosilylation and hydroboration in a sustainable manner: from Earth-abundant catalysts to catalyst-free solutions. Green Chemistry 2020, 22, 5210 -5224.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Hydrosilylation and hydroboration in a sustainable manner: from Earth-abundant catalysts to catalyst-free solutions. Green Chemistry. 2020; 22 (16):5210-5224.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2020. "Hydrosilylation and hydroboration in a sustainable manner: from Earth-abundant catalysts to catalyst-free solutions." Green Chemistry 22, no. 16: 5210-5224.
The formation of several silyl ethers (alkoxysilanes, R 3 Si‐OR’) and unsymmetrical siloxanes (R 3 Si‐O‐SiR’ 3 ) can be catalyzed by the commercially available potassium bis(trimethylsilyl)amide (KHMDS). The reaction proceeds via direct dealkynative coupling between various alcohols or silanols and alkynylsilanes, with a simultaneous formation of gaseous acetylene as the sole by‐product. The dehydrogenative and dealkenative coupling of alcohols or silanols are well‐investigated, whilst the utilization of alkynylsilanes as silylating agents has never been comprehensively studied in this context. Overall, the presented system allows the synthesis of various attractive organosilicon compounds under mild conditions, making this approach an atom‐efficient, environmentally benign, and sustainable alternative to existing synthetic solutions.
Krzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes - an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes. European Journal of Organic Chemistry 2020, 2020, 4042 -4049.
AMA StyleKrzysztof Kuciński, Hanna Stachowiak, Grzegorz Hreczycho. Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes - an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes. European Journal of Organic Chemistry. 2020; 2020 (26):4042-4049.
Chicago/Turabian StyleKrzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. 2020. "Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes - an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes." European Journal of Organic Chemistry 2020, no. 26: 4042-4049.
A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at rt under mild conditions.
Krzysztof Kuciński; Grzegorz Hreczycho. Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols. European Journal of Organic Chemistry 2020, 2020, 552 -555.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols. European Journal of Organic Chemistry. 2020; 2020 (5):552-555.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2020. "Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols." European Journal of Organic Chemistry 2020, no. 5: 552-555.
A simple and highly practical Amberlyst-catalyzed direct O-metalation of silanols, POSS silanols and alkoxysilanes under mild conditions is proposed. This protocol can be applied to the synthesis of a wide range of important organosilicon derivatives such as siloxanes, germasiloxanes, borasiloxanes and functionalized silsesquioxanes. It is worth noting that Amberlyst-15 can be reused for further experiments and its catalytic activity in this process is well-preserved for several recycling steps.
Krzysztof Kuciński; Grzegorz Hreczycho. O-Metalation of silanols and POSS silanols over Amberlyst-15 catalyst: A facile route to unsymmetrical siloxanes, borasiloxanes and germasiloxanes. Inorganica Chimica Acta 2019, 490, 261 -266.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. O-Metalation of silanols and POSS silanols over Amberlyst-15 catalyst: A facile route to unsymmetrical siloxanes, borasiloxanes and germasiloxanes. Inorganica Chimica Acta. 2019; 490 ():261-266.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2019. "O-Metalation of silanols and POSS silanols over Amberlyst-15 catalyst: A facile route to unsymmetrical siloxanes, borasiloxanes and germasiloxanes." Inorganica Chimica Acta 490, no. : 261-266.
Lithium triethylborohydride as an efficient and easily accessible catalyst for hydroboration of numerous carbonyls under solvent-free conditions at room temperature.
Krzysztof Kuciński; Grzegorz Hreczycho. Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones. Green Chemistry 2019, 21, 1912 -1915.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones. Green Chemistry. 2019; 21 (8):1912-1915.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2019. "Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones." Green Chemistry 21, no. 8: 1912-1915.
A commercially available and stable ruthenium dodecacarbonyl catalyst (Ru3(CO)12) allows very efficient and convenient access to functionalized silsesquioxanes (SQs) containing siloxane moiety (Si–O–Si) via dehydrogenative coupling of POSS-silanols with hydrosilanes. With the aid of SiH-containing silsesquioxanes, an unprecedented one-pot procedure has been revealed, and the usefulness of this approach was demonstrated by the synthesis of various derivatives via O-silylation, as well as C═C and C═N hydrosilylation.
Joanna Kaźmierczak; Krzysztof Kuciński; Dariusz Lewandowski; Grzegorz Hreczycho. Ru-Catalyzed Dehydrogenative Silylation of POSS-Silanols with Hydrosilanes: Its Introduction to One-Pot Synthesis. Inorganic Chemistry 2019, 58, 1201 -1207.
AMA StyleJoanna Kaźmierczak, Krzysztof Kuciński, Dariusz Lewandowski, Grzegorz Hreczycho. Ru-Catalyzed Dehydrogenative Silylation of POSS-Silanols with Hydrosilanes: Its Introduction to One-Pot Synthesis. Inorganic Chemistry. 2019; 58 (2):1201-1207.
Chicago/Turabian StyleJoanna Kaźmierczak; Krzysztof Kuciński; Dariusz Lewandowski; Grzegorz Hreczycho. 2019. "Ru-Catalyzed Dehydrogenative Silylation of POSS-Silanols with Hydrosilanes: Its Introduction to One-Pot Synthesis." Inorganic Chemistry 58, no. 2: 1201-1207.
Versatile direct Hiyama‐type C‐H arylations of benzamides were accomplished with organosiloxanes by chelation‐ assisted cobalt catalysis. The C‐H arylation featured broad substrate scope, including challenging C(sp3)–H activation, the use of GVL as biomass‐derived solvent, and selectively provided the desired biaryls, even when being highly sterically hindered.
Qingqing Bu; Elżbieta Gońka; Krzysztof Kuciński; Lutz Ackermann. Cobalt‐Catalyzed Hiyama‐type C‐H Activation with Arylsiloxanes: Versatile Access to Highly‐Ortho‐Decorated Biaryls. Chemistry – A European Journal 2018, 25, 2213 -2216.
AMA StyleQingqing Bu, Elżbieta Gońka, Krzysztof Kuciński, Lutz Ackermann. Cobalt‐Catalyzed Hiyama‐type C‐H Activation with Arylsiloxanes: Versatile Access to Highly‐Ortho‐Decorated Biaryls. Chemistry – A European Journal. 2018; 25 (9):2213-2216.
Chicago/Turabian StyleQingqing Bu; Elżbieta Gońka; Krzysztof Kuciński; Lutz Ackermann. 2018. "Cobalt‐Catalyzed Hiyama‐type C‐H Activation with Arylsiloxanes: Versatile Access to Highly‐Ortho‐Decorated Biaryls." Chemistry – A European Journal 25, no. 9: 2213-2216.
A simple and highly practical catalyst‐free O‐silylation of silanols with commercially available disilazanes has been developed under mild conditions. In the case of POSS silanols and some silanols, it is necessary to use catalytic amounts of inexpensive bismuth(III) triflate as additional catalyst. This efficient chlorine‐free protocol involves the synthesis of a wide range of important organosilicon derivatives such as unsymmetrical disiloxanes and functionalized silsesquioxanes.
Krzysztof Kuciński; Grzegorz Hreczycho. A Highly Effective Route to Si−O−Si Moieties through O ‐Silylation of Silanols and Polyhedral Oligomeric Silsesquioxane Silanols with Disilazanes. ChemSusChem 2018, 12, 1043 -1048.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. A Highly Effective Route to Si−O−Si Moieties through O ‐Silylation of Silanols and Polyhedral Oligomeric Silsesquioxane Silanols with Disilazanes. ChemSusChem. 2018; 12 (5):1043-1048.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2018. "A Highly Effective Route to Si−O−Si Moieties through O ‐Silylation of Silanols and Polyhedral Oligomeric Silsesquioxane Silanols with Disilazanes." ChemSusChem 12, no. 5: 1043-1048.
In this paper, the Pt-catalyzed hydrosilylation of hydroxyl ethers is described. Various bifunctional alkoxysilanes were obtained and applied in O-silylation of free hydroxyl groups on the silica surface. These modified solid materials have been used as excellent supports for linking synthetic nucleic acids. Nucleic acids permanently attached to the solid surface were tested in hybridization with complementary fluorescence-labeled sequences. Detection of nucleic acids anchored to the solid support was performed by fluorescence microscopy after hybridization.
Krzysztof Kuciński; Magdalena Jankowska-Wajda; Tomasz Ratajczak; Sandra Bałabańska-Trybuś; Anna Schulmann; Hieronim Maciejewski; Marcin K. Chmielewski; Grzegorz Hreczycho. Silica Surface Modification and Its Application in Permanent Link with Nucleic Acids. ACS Omega 2018, 3, 5931 -5937.
AMA StyleKrzysztof Kuciński, Magdalena Jankowska-Wajda, Tomasz Ratajczak, Sandra Bałabańska-Trybuś, Anna Schulmann, Hieronim Maciejewski, Marcin K. Chmielewski, Grzegorz Hreczycho. Silica Surface Modification and Its Application in Permanent Link with Nucleic Acids. ACS Omega. 2018; 3 (6):5931-5937.
Chicago/Turabian StyleKrzysztof Kuciński; Magdalena Jankowska-Wajda; Tomasz Ratajczak; Sandra Bałabańska-Trybuś; Anna Schulmann; Hieronim Maciejewski; Marcin K. Chmielewski; Grzegorz Hreczycho. 2018. "Silica Surface Modification and Its Application in Permanent Link with Nucleic Acids." ACS Omega 3, no. 6: 5931-5937.
This paper demonstrates an efficient, mild and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acylating agent. During our tests, we also investigated the differences in the activity between metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion® as heterogeneous catalyst of S-acetylation of thiols.
Krzysztof Kuciński; Grzegorz Hreczycho. S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters. Organic Process Research & Development 2018, 22, 489 -493.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters. Organic Process Research & Development. 2018; 22 (4):489-493.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2018. "S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters." Organic Process Research & Development 22, no. 4: 489-493.
For the first time, a general method for catalyst-free and solvent-free hydroboration of various aldehydes has been developed.
Hanna Stachowiak; Joanna Kaźmierczak; Krzysztof Kuciński; Grzegorz Hreczycho. Catalyst-free and solvent-free hydroboration of aldehydes. Green Chemistry 2018, 20, 1738 -1742.
AMA StyleHanna Stachowiak, Joanna Kaźmierczak, Krzysztof Kuciński, Grzegorz Hreczycho. Catalyst-free and solvent-free hydroboration of aldehydes. Green Chemistry. 2018; 20 (8):1738-1742.
Chicago/Turabian StyleHanna Stachowiak; Joanna Kaźmierczak; Krzysztof Kuciński; Grzegorz Hreczycho. 2018. "Catalyst-free and solvent-free hydroboration of aldehydes." Green Chemistry 20, no. 8: 1738-1742.
Due to their versatile applications silsesquioxanes (SQs) are of considerable interest for creating hybrid inorganic-organic materials. In this report, two novel and independent strategies for the direct attachment of boron functionalities to silsesquioxanes are presented. Encouraged by our previous work concerning the synthesis of borasiloxanes through the catalyst-free dehydrogenative coupling of silanols and boranes, we decided to apply our method to a synthesis of various boron-functionalized silsesquioxanes. During our tests, we also investigated the activity of scandium(III) triflate, which we have previously used as an excellent catalyst for the obtaining of Si-O-Si and Si-O-Ge moieties. As a result, we also discovered a novel approach for the O-borylation of Si-OH groups in silsesquioxanes with allylborane. Both routes are highly chemoselective and efficiently lead to the obtaining of Si-O-B moiety under air atmosphere and at rt.
Joanna Kaźmierczak; Krzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. Introduction of Boron Functionalities into Silsesquioxanes: Novel Independent Methodologies. Chemistry – A European Journal 2018, 24, 2509 -2514.
AMA StyleJoanna Kaźmierczak, Krzysztof Kuciński, Hanna Stachowiak, Grzegorz Hreczycho. Introduction of Boron Functionalities into Silsesquioxanes: Novel Independent Methodologies. Chemistry – A European Journal. 2018; 24 (10):2509-2514.
Chicago/Turabian StyleJoanna Kaźmierczak; Krzysztof Kuciński; Hanna Stachowiak; Grzegorz Hreczycho. 2018. "Introduction of Boron Functionalities into Silsesquioxanes: Novel Independent Methodologies." Chemistry – A European Journal 24, no. 10: 2509-2514.
This paper demonstrates the first highly chemoselective syntheses of various borasiloxanes from hydroboranes and silanols, achieved through catalyst-free dehydrogenative coupling at room temperature. This green protocol, which uses easily accessible reagents, allows for the obtaining of borasiloxanes under air atmosphere and solvent-free conditions.
K. Kuciński; G. Hreczycho. Chemoselective and Catalyst-Free O-Borylation of Silanols: A Facile Access to Borasiloxanes. ChemSusChem 2017, 10, 4695 -4698.
AMA StyleK. Kuciński, G. Hreczycho. Chemoselective and Catalyst-Free O-Borylation of Silanols: A Facile Access to Borasiloxanes. ChemSusChem. 2017; 10 (23):4695-4698.
Chicago/Turabian StyleK. Kuciński; G. Hreczycho. 2017. "Chemoselective and Catalyst-Free O-Borylation of Silanols: A Facile Access to Borasiloxanes." ChemSusChem 10, no. 23: 4695-4698.
Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S-benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol-%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.
Krzysztof Kuciński; Grzegorz Hreczycho. Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate. European Journal of Organic Chemistry 2017, 2017, 5572 -5581.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate. European Journal of Organic Chemistry. 2017; 2017 (37):5572-5581.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2017. "Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate." European Journal of Organic Chemistry 2017, no. 37: 5572-5581.
Krzysztof Kuciński; Grzegorz Hreczycho. Ruthenium-catalyzed hydrosilylation of C=N bond in benzothiazole. Journal of Organometallic Chemistry 2017, 846, 321 -325.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Ruthenium-catalyzed hydrosilylation of C=N bond in benzothiazole. Journal of Organometallic Chemistry. 2017; 846 ():321-325.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2017. "Ruthenium-catalyzed hydrosilylation of C=N bond in benzothiazole." Journal of Organometallic Chemistry 846, no. : 321-325.
Silsesquioxanes (POSS) have recently become the subject of growing interest in many branches of materials chemistry. Despite this great interest, no direct metal-catalyzed method to cap the corner of the POSS molecules has yet been proposed. In this report, we present a highly efficient method for the synthesis of functionalized silsesquioxanes mediated by scandium(III) triflate, which opens up the possibility of introducing a wide variety of functional groups into this class of organosilicon compounds under mild conditions with excellent yields. We also investigated the differences in the activity of the Lewis acid (Sc(OTf)3) and the hidden Brønsted acid (TfOH) generated in situ from triflates as catalysts in the functionalization of silsesquioxanes. What is more, this solution provides an efficient corner-capping reaction and other functionalizations to obtain silsesquioxane derivatives which are often not possible to synthesize with good yields, efficiency, and chemoselectivity using conventional methods.
Joanna Kaźmierczak; Krzysztof Kuciński; Grzegorz Hreczycho. Highly Efficient Catalytic Route for the Synthesis of Functionalized Silsesquioxanes. Inorganic Chemistry 2017, 56, 9337 -9342.
AMA StyleJoanna Kaźmierczak, Krzysztof Kuciński, Grzegorz Hreczycho. Highly Efficient Catalytic Route for the Synthesis of Functionalized Silsesquioxanes. Inorganic Chemistry. 2017; 56 (15):9337-9342.
Chicago/Turabian StyleJoanna Kaźmierczak; Krzysztof Kuciński; Grzegorz Hreczycho. 2017. "Highly Efficient Catalytic Route for the Synthesis of Functionalized Silsesquioxanes." Inorganic Chemistry 56, no. 15: 9337-9342.
Silicon and its compounds with other heteroatoms have received considerable attention, particularly because of their applicative ability. Silicon forms a large number of compounds with other p-block elements (e.g., C, N, S, O, F, Cl, and others). All of them affect practical chemistry to some extent and are characterized by unique properties. This article highlights recent developments and covers the literature from the last 10 years. It is mainly focused on catalytic methods for silicon–nitrogen, silicon–phosphorus, silicon–oxygen, and silicon–sulfur bond formation. The scope and applications of these practical compounds will also be discussed.
Krzysztof Kuciński; Grzegorz Hreczycho. Catalytic Formation of Silicon-Heteroatom (N, P, O, S) Bonds. ChemCatChem 2017, 9, 1868 -1885.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Catalytic Formation of Silicon-Heteroatom (N, P, O, S) Bonds. ChemCatChem. 2017; 9 (11):1868-1885.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2017. "Catalytic Formation of Silicon-Heteroatom (N, P, O, S) Bonds." ChemCatChem 9, no. 11: 1868-1885.
Krzysztof Kuciński; Grzegorz Hreczycho. Synthesis of novel bifunctional organosilicon dendrons via platinum-catalyzed hydrosilylation. Inorganica Chimica Acta 2017, 461, 233 -238.
AMA StyleKrzysztof Kuciński, Grzegorz Hreczycho. Synthesis of novel bifunctional organosilicon dendrons via platinum-catalyzed hydrosilylation. Inorganica Chimica Acta. 2017; 461 ():233-238.
Chicago/Turabian StyleKrzysztof Kuciński; Grzegorz Hreczycho. 2017. "Synthesis of novel bifunctional organosilicon dendrons via platinum-catalyzed hydrosilylation." Inorganica Chimica Acta 461, no. : 233-238.