A Heterogeneous Iridium Catalyst for the Hydroboration of Pyridines DOI

Jessica Rodriguez,

Matthew P. Conley

Organic Letters, Journal Year: 2022, Volume and Issue: 24(25), P. 4680 - 4683

Published: June 16, 2022

Sulfated zirconium oxide (SZO) capped with silylium-like ions reacts (cod)Ir(py)Cl (cod = 1,5-cyclooctadiene; py pyridine) to form [Ir(cod)py][SZO] (1) and Me3SiCl. 1 can also be formed in reactions of phosphonium functionalized SZO [Ir(cod)(OSi(OtBu)3]2, which forms [Ir(cod)P(tBu)2Ph][SZO] (2), followed by reaction pyridine 1. FTIR 15N{1H} MAS NMR spectroscopy are consistent coordination an electrophilic iridium. is moderately active the dearomative hydroboration pyridine. The primary product this 1,2-dihydropyridine, converts 1,4-dihydropyridine at long times. catalyzes a variety substituted pyridines reactive toward pyrazines N-methylimidazole.

Language: Английский

Repurposing a supramolecular iridium catalyst via secondary Zn⋯OC weak interactions between the ligand and substrate leads to ortho-selective C(sp2)–H borylation of benzamides with unusual kinetics DOI Creative Commons
Jonathan Trouvé,

Vanessa Delahaye,

Michele Tomasini

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(30), P. 11794 - 11806

Published: Jan. 1, 2024

Supramolecular catalysts based on a zinc-porphyrin molecular recognition site and catalytically active iridium enabled the selective ortho -C–H borylation of benzamides under regime in which C–H activation step is not rate-determining.

Language: Английский

Citations

2
Hydroboration of Terminal Alkynes Catalyzed by a Mn(I) Alkyl PCP Pincer Complex Following Two Diverging Pathways DOI Creative Commons
Daniel Zobernig, Berthold Stöger, Luı́s F. Veiros

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12385 - 12391

Published: Aug. 5, 2024

A stereo- and regioselective Mn(I)-catalyzed hydroboration of terminal alkynes with pinacolborane (HBPin) is described. The reaction highly

Language: Английский

Citations

2
Selective Benzylic CH‐Borylations by Tandem Cobalt Catalysis DOI
Pradip Ghosh, Roland Schoch, Matthias Bauer

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(1)

Published: Oct. 1, 2021

Metal-catalyzed C-H activations are environmentally and economically attractive synthetic strategies for the construction of functional molecules as they obviate need pre-functionalized substrates minimize waste generation. Great challenges reside in control selectivities, utilization unbiased hydrocarbons, operation atom-economical dehydrocoupling mechanisms. An especially mild borylation benzylic CH bonds was developed with ligand-free pre-catalyst Co[N(SiMe

Language: Английский

Citations

16
A review of the R3Si–NH–SiR3–type disilazanes: From synthesis to applications DOI Creative Commons
Krzysztof Kuciński, Hanna Stachowiak, Dariusz Lewandowski

et al.

Journal of Organometallic Chemistry, Journal Year: 2021, Volume and Issue: 961, P. 122127 - 122127

Published: Oct. 19, 2021

Disilazanes (e.g., hexamethyldisilazane, tetramethyldisilazane, etc.) are a group of compounds containing direct silicon-nitrogen bond, which can be easily cleavage and finally resulted in their usefulness as the source nitrogen multicomponent reactions) or silicon O–silylation). This review focuses on synthesis further applications from last twenty years. Whilst use these disilazanes silylating agents is well-known, incorporation into organic molecules offers immense, but still unexplored opportunities synthetic chemistry. Last not least, indirect involvement catalysis also shortly discussed.

Language: Английский

Citations

15
A Heterogeneous Iridium Catalyst for the Hydroboration of Pyridines DOI

Jessica Rodriguez,

Matthew P. Conley

Organic Letters, Journal Year: 2022, Volume and Issue: 24(25), P. 4680 - 4683

Published: June 16, 2022

Sulfated zirconium oxide (SZO) capped with silylium-like ions reacts (cod)Ir(py)Cl (cod = 1,5-cyclooctadiene; py pyridine) to form [Ir(cod)py][SZO] (1) and Me3SiCl. 1 can also be formed in reactions of phosphonium functionalized SZO [Ir(cod)(OSi(OtBu)3]2, which forms [Ir(cod)P(tBu)2Ph][SZO] (2), followed by reaction pyridine 1. FTIR 15N{1H} MAS NMR spectroscopy are consistent coordination an electrophilic iridium. is moderately active the dearomative hydroboration pyridine. The primary product this 1,2-dihydropyridine, converts 1,4-dihydropyridine at long times. catalyzes a variety substituted pyridines reactive toward pyrazines N-methylimidazole.

Language: Английский

Citations

11