Reevaluating ortho-Carborane Synthesis: Success with Mono-Substituted Acetylenes in the Presence of Silver Salts

The study shows that traditional methods for synthesizing ortho-carboranes from nido-B10H14 and its complexes (B10H12L2) using donor- and acceptor-disubstituted acetylenes yielding low efficiencies (yields 0 - 12%). Attempts to improve yields with ionic liquids and silver salts as catalysts were unsuccessful with disubstituted acetylenes. However, it has been found that the use of mono-substituted acetylenes (phenylacetylene, ethyl propiolate) in the presence of silver salts in the reaction with B10H12L2 substrates produces ortho-carboranes in high yields (~90%). This suggests that the key step is the formation and subsequent addition of silver acetylenides, and not the donor-acceptor π-complexes previously assumed. This finding allows us to better understand the mechanisms of the ortho-carboranes formation and offers an efficient pathway for their synthesis.

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Publication Details

Journal
Journal of organic and pharmaceutical chemistry
Published
2024-12-23
DOI
https://doi.org/10.24959/ophcj.24.316200
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Reevaluating ortho-Carborane Synthesis: Success with Mono-Substituted Acetylenes in the Presence of Silver Salts

Radomyr V. Smaliy, Alexander Pashenko, Alona S. Cherednichenko, Yulian L. Lishchenko et al.
Journal of organic and pharmaceutical chemistry
Boron Compounds in Chemistry
article

Reevaluating ortho-Carborane Synthesis: Success with Mono-Substituted Acetylenes in the Presence of Silver Salts

Radomyr V. Smaliy, Alexander Pashenko, Alona S. Cherednichenko, Yulian L. Lishchenko, Artem M. Mishchenko, Nataliya A. Shtil, Andrey P. Mityuk, Yuliya V. Rassukana, Oleh V. Svaliavyn, Volodymyr V. Turcheniuk
article en

Abstract

The study shows that traditional methods for synthesizing ortho-carboranes from nido-B10H14 and its complexes (B10H12L2) using donor- and acceptor-disubstituted acetylenes yielding low efficiencies (yields 0 - 12%). Attempts to improve yields with ionic liquids and silver salts as catalysts were unsuccessful with disubstituted acetylenes. However, it has been found that the use of mono-substituted acetylenes (phenylacetylene, ethyl propiolate) in the presence of silver salts in the reaction with B10H12L2 substrates produces ortho-carboranes in high yields (~90%). This suggests that the key step is the formation and subsequent addition of silver acetylenides, and not the donor-acceptor π-complexes previously assumed. This finding allows us to better understand the mechanisms of the ortho-carboranes formation and offers an efficient pathway for their synthesis.

Journal of organic and pharmaceutical chemistryVol. 22(3)
National Academy of Sciences of Ukraine (UA), Taras Shevchenko National University of Kyiv (UA), National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute” (UA), Institute of Organic Chemistry (UA), Enamine (Ukraine) (UA)
National Research Foundation of Ukraine, National Research Foundation
Openalex Percentile: Top 59%
Boron Compounds in Chemistry
DOIOpen Access PDFOpenAlex
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