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Keywords = phosphino-borane

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14 pages, 3174 KiB  
Article
Non-Selective Reduction of P-Stereogenic Phosphinoylacetic Acid Esters and 3-Phosphorylated Coumarins to Phosphino-Boranes: Discovery of Unexpected 2,3-Dihydrobenzofuran Derivative
by Kamil Dziuba, Natalia Walczak and Katarzyna Szwaczko
Symmetry 2024, 16(8), 976; https://doi.org/10.3390/sym16080976 - 1 Aug 2024
Viewed by 1602
Abstract
This paper presents the efficient reduction of phosphinoylacetic acid esters and 3-phosphorylated coumarin to their corresponding phosphino-boranes using BH₃-THF complexes. Optimized conditions for the reduction of phosphinoylacetic acid esters resulted in high yields of phosphinoborates. The straightforwardness and efficiency of the process were [...] Read more.
This paper presents the efficient reduction of phosphinoylacetic acid esters and 3-phosphorylated coumarin to their corresponding phosphino-boranes using BH₃-THF complexes. Optimized conditions for the reduction of phosphinoylacetic acid esters resulted in high yields of phosphinoborates. The straightforwardness and efficiency of the process were demonstrated for diarylphosphinoylacetic acid ethyl esters, as well as P-stereogenic L-menthyl esters, where the simultaneous reduction of the strong P=O bond and the ester group was exclusively observed for the first time. The study also highlighted the significant influence of steric effects with bulky substituents, such as the menthol group or the 1-naphthyl substituent at phosphorus, on the reduction efficiency. However, the reduction of 3-phosphorylated coumarins produced an unexpected reaction product: a 2,3-dihydrobenzofuran derivative. The present findings provide valuable information on the direct reduction of phosphine oxides and related compounds, demonstrating the versatility of borane complexes in synthetic chemistry, and provide new perspectives for studying the problems of symmetry and asymmetry in the chemistry of such transformations. Full article
(This article belongs to the Collection Feature Papers in Chemistry)
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15 pages, 2711 KiB  
Article
Mono-Alkyl-Substituted Phosphinoboranes (HRP–BH2–NMe3) as Precursors for Poly(alkylphosphinoborane)s: Improved Synthesis and Comparative Study
by Felix Lehnfeld, Tim Oswald, Rüdiger Beckhaus and Manfred Scheer
Inorganics 2023, 11(10), 377; https://doi.org/10.3390/inorganics11100377 - 23 Sep 2023
Cited by 2 | Viewed by 1939
Abstract
A new synthetic pathway to various mono-alkyl-substituted phosphinoboranes HRP–BH2–NMe3 has been developed. The new synthetic route starting from alkyl halides and NaPH2 followed by metalation and salt metathesis is performed in a one-pot procedure and leads to higher yields [...] Read more.
A new synthetic pathway to various mono-alkyl-substituted phosphinoboranes HRP–BH2–NMe3 has been developed. The new synthetic route starting from alkyl halides and NaPH2 followed by metalation and salt metathesis is performed in a one-pot procedure and leads to higher yields and purity of the resulting phosphinoboranes, as compared to previously reported routes. Additionally, the scope of accessible compounds could be expanded from short-chained linear alkyl substituents to longer-chained linear alkyl substituents as well as secondary or functionalized alkyl substituents. The reported examples include primary alkyl-substituted phosphinoboranes RHP-BH2-NMe3 (R = n-butyl, n-pentyl, n-hexyl; 1a–c), the secondary alkyl-substituted derivatives iPrPH-BH2-NMe3 (2), and the functionalized alkyl-substituted 4-bromo-butyl-phosphinoborane (BrC4H8)PH-BH2-NMe3 (3). Compounds 1a, 1c, and 2 were additionally used for preliminary polymerization reactions via a thermal and a transition metal-catalyzed pathway, revealing the formation of high-molecular-weight polymers under certain conditions. Detailed investigations on the influence of temperature, concentration, substituents and reaction time on the respective polymerization reactions were performed. Full article
(This article belongs to the Special Issue 10th Anniversary of Inorganics: Organometallic Chemistry)
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