Synthesis and Evaluation of Ruthenium 2‐Alkyl‐6‐mercaptophenolate Catalysts for Olefin Metathesis

Wang, Tao; Yu, Xiaobo; Zhang, Huiqing; Wu, Shao-Hua; Guo, Weijie; Wang, Jianhui

doi:10.1002/aoc.4939

Cited by 5 publications

(2 citation statements)

References 34 publications

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“…The synthesis of 1,4-S 2 -DBD dyes turned out to be difficult and is based on a Pd-catalyzed intramolecular oxidative C–H-sulfuration. 33 34 Starting with compound 48 ( cf. Scheme 8 ) the thiocarbamate 56 is prepared.…”

Section: Synthesismentioning

confidence: 99%

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Wessig¹,

Lehmann²

2023

Synthesis

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In this review we give an overview of the syntheses and photophysical properties of the new class of fluorescent dyes based on a [1,3]-dioxolo[4,5-f]benzodioxole core and their derivatives. Starting from commercially available reactants (e.g., sesamol, 1,2,4,5-tetrachlorobenzene) the core units can be prepared in a simple manner. Then, the benzene core can be derivatized via lithiation and their photophysical properties can be adjusted as desired. The obtained fluorophores have an absorption range of 403–520 nm and an emission range of 495–665 nm. This class of fluorescent dyes is also characterized by a long fluorescence lifetime, a high stability towards photobleaching, large Stokes shifts, and small size. Thus, the DBD dyes are optimally suited for optical sensing.1 Introduction2 Synthesis3 Properties4 Applications

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Section: Synthesismentioning

confidence: 99%

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Wessig¹,

Lehmann²

2023

Synthesis

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“…This was the first example of a Ru-based catalyst with high Z-selectivity in cross-metathesis reactions (>95%) [13]. This breakthrough prompted researchers to create new catalytic systems that access a Z-preference over the E-preference [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Role of Electronic and Steric Effects on Ruthenium Catalysts with Bulky NHC Ligands and Relationship with the Z-Selectivity in Olefin Metathesis

Diaz-González,

Paredes-Gil

2023

Catalysts

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Recently, sterically demanding N-heterocyclic cyclometalated ruthenium were reported as efficient Z-selective catalysts for cross-metathesis, showing a different reactivity in the function of the auxiliary ligand and the bulky ligand. To understand the origin of this behavior, we carried out density functional (M06-L) calculations to explore the reaction mechanism and insight from the energetic contributions into the determinant step. We emphasize the differences that occur when the 2,6-diisopropylphenyl (Dipp) and 2,6-diisopentylphenyl (Dipep) are employed. The results show that the barrier energies, ΔG‡, increase when the bulky ligand is greater, using nitrate as an auxiliary ligand, while the opposite behavior is obtained when pivalate is the auxiliary ligand. This tendency has its origin in the low reorganization energy and the less steric hindrance (%Vbur) obtained in catalysts that involve nitrate ligand and Dipep group. Moreover, by scrutinizing the energy decomposition analysis (EDA), it is found that the electronic contributions are also dominant and are not uniquely the steric effects that control the Z-selectivity.

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Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

et al. 2020

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Dedicated to Professor Bernd Giese on the occasion of his 80th birthday. The replacement of oxygen by sulfur atoms of [1,3]-dioxolo[4.5f]benzodioxole (DBD) fluorescent dyes is an efficient way to adjust the photophysical properties (sulfur tuning). While previously developed S 4-DBD dyes exhibit considerably redshifted absorption and emission wavelength, the heavy atom effect of four sulfur atoms cause low fluorescence quantum yields and short fluorescence lifetimes. Herein, we demonstrate that the replacement of less than four sulfur atoms (S 1-DBD, 1,2-S 2-DBD, and 1,4-S 2-DBD dyes) permits a fine-tuning of the photophysical properties. In some cases, a similar influence on the wavelength without the detrimental effect on the quantum yields and lifetimes is observed. Furthermore, the synthetic accessibility of S 1-and S 2-DBD dyes is improved, compared with S 4-DBD dyes. For coupling with biomolecules a series of reactive derivatives of the new dyes were developed (azides, OSu esters, alkynes, maleimides).

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Synthesis and Evaluation of Ruthenium 2‐Alkyl‐6‐mercaptophenolate Catalysts for Olefin Metathesis

Cited by 5 publications

References 34 publications

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Role of Electronic and Steric Effects on Ruthenium Catalysts with Bulky NHC Ligands and Relationship with the Z-Selectivity in Olefin Metathesis

Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

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