From Hydroborations Catalyzed by Sn(II) Cations to Photoluminescent Boronic Esters

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F25%3A39923336" target="_blank" >RIV/00216275:25310/25:39923336 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/cctc.202500462" target="_blank" >https://doi.org/10.1002/cctc.202500462</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cctc.202500462" target="_blank" >10.1002/cctc.202500462</a>

Result language
angličtina
Original language name
From Hydroborations Catalyzed by Sn(II) Cations to Photoluminescent Boronic Esters
Original language description
The N-coordinated Sn(II) cations [{(2,6-iPr2-C6H3)-N = C(Me)-(6-MeO)-C5H3N}SnCl](SnCl3) (1), [{(2,6-iPr2-C6H3)-N = C(Me)-(6-P(O)(OiPr)2)-C5H3N}SnCl](SnCl3) (2), and [{(1,2-(C5H4N-2-CH = N)2CH2CH2)}SnCl](SnCl3) (3) were prepared and used as catalysts in the hydroboration of ketones and aldehydes. Mechanistic and kinetic studies provide evidence that these electrophiles interact with the C & boxH;O bond of the substrates and indicate a pseudo-first-order reaction with a rate constant of k = 70.2 h-1 using 2 mol% of 1. 1 could effectively be used as a catalyst in the hydroboration of a broad range of substrates including, substituted benzaldehydes, heterocyclic carbaldehydes, and aliphatic aldehydes, as well as ketones. Finally, 1 was used in large-scale hydroboration reactions of pyridine-substituted carbaldehydes to prepare the respective pyridine-substituted boronic esters [2-(PinBOCH2)-C5H4N] (4), [2-(PinBOCH2)-4-(MeO)-C5H3N] (5), [2-(PinBOCH2)-6-(MeO)-C5H3N] (6), [2-(PinBOCH2)-6-Br-C5H3N] (7), [2-(PinBOCH2)-5-Br-C5H3N] (8), [3-(PinBOCH2)-C5H4N] (9), and borinate [2-[(BBN)OCH2]-4-(MeO)-C5H3N] (10), which were characterized by NMR spectroscopy, single-crystal X-ray structure analysis, and an analysis of their photoluminescence.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10400 - Chemical sciences

Project
<a href="/en/project/EH23_021%2F0008593" target="_blank" >EH23_021/0008593: Innovative materials with high added value suitable for applications</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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