A Photocatalytic C(sp)–B Bond Formation Employing SOMOphilic Alkynyl Sulfones and Nucleophilic Boryl Radicals

Abstract Alkynylboron compounds are important scaffolds with broad applicability in organic synthesis. In contrast to polar or metal-catalyzed processes, here a radical approach is employed for the addition of nucleophilic boryl radicals to electrophilic SOMOphiles for the construction of the C(sp)–B bond. The reaction renders the corresponding alkynylated amine boranes with broad functional group compatibility. In addition, theoretical studies have been carried out by means of DFT to understand the reactivity and selectivity of the addition process.

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Publication Details

Journal
Synthesis
Published
2024-11-08
DOI
https://doi.org/10.1055/a-2464-8904
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.00

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article

A Photocatalytic C(sp)–B Bond Formation Employing SOMOphilic Alkynyl Sulfones and Nucleophilic Boryl Radicals

Eva Rivera‐Chao, Javier Corpas, Enrique M. Arpa, Luka Obradović
4 citations
Synthesis
Sulfur-Based Synthesis Techniques
1.00
article

A Photocatalytic C(sp)–B Bond Formation Employing SOMOphilic Alkynyl Sulfones and Nucleophilic Boryl Radicals

Eva Rivera‐Chao, Javier Corpas, Enrique M. Arpa, Luka Obradović
article en
4 citations

Abstract

Abstract Alkynylboron compounds are important scaffolds with broad applicability in organic synthesis. In contrast to polar or metal-catalyzed processes, here a radical approach is employed for the addition of nucleophilic boryl radicals to electrophilic SOMOphiles for the construction of the C(sp)–B bond. The reaction renders the corresponding alkynylated amine boranes with broad functional group compatibility. In addition, theoretical studies have been carried out by means of DFT to understand the reactivity and selectivity of the addition process.

SynthesisVol. 57(17)
RWTH Aachen University (DE)
H2020 Marie Skłodowska-Curie Actions
Clean water and sanitation
Openalex Percentile: Top 26%
Sulfur-Based Synthesis Techniques
1.00
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