Secondary Thioamides as Multidentate Ligands for Functional Metal Complexes

Kuwabara, Junpei; Kanbara, Takaki

doi:10.1246/cl.140996

Cited by 24 publications

(15 citation statements)

References 74 publications

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“…Thioamide compounds are one of the most attractive molecules in pharmaceuticals, agrochemicals, electronic chemicals and material sciences [16][17][18][19][20][21][22]. In coordination chemistry, pincer-type ligands containing thio-amide motif have already exhibited their 4 incomparable chelating ability to the selected transition-metals, and their corresponding complexes have been applied in various areas such as chemical-sensor materials, tunable redox-potential complexes, polymer hybrid luminescence materials, building blocks for multinuclear com-plexes, and catalysts for cross-coupling reactions [23][24][25][26][27][28][29][30]. The thio-substitution of amides with LR is an efficient and straightforward method, either the availability of amide substrates, LR, or the reaction condition [7,8,[31][32][33][34][35].…”

Section: Figure 1 Generation Of the Six-membered By-product Amentioning

confidence: 99%

A Column-Free and Aqueous Waste-Free Process for Thioamide Preparation with Lawesson’s reagent

Ke¹,

Ling²,

Ding³

et al. 2020

Preprint

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After completing thio-substitution with the Lawesson’s reagent, ethanol was found to be able to efficiently decompose the inherent stoichiometric six-membered-ring by-product from the Lawesson’s reagent to a highly polarized diethyl thiophosphate. This treatment could significantly simplify the following column purification of the desired thioamide in a small scale preparation. As scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including traditional phase-cut, extraction, and re-crystallization. The newly developed column-free procedure did not generate P-contained aqueous waste, and only organic effluents were discharged. It was believed that the optimized procedure can greatly provide opportunity of the application of the Lawesson’s reagent for various thio-substituted reacions in scaling up preparation.

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Section: Figure 1 Generation Of the Six-membered By-product Amentioning

confidence: 99%

A Column-Free and Aqueous Waste-Free Process for Thioamide Preparation with Lawesson’s reagent

Ke¹,

Ling²,

Ding³

et al. 2020

Preprint

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show abstract

“…After the first family of PCP complexes was synthetized by Shaw in 1976 [7], numerous research groups have applied this concept for almost all types of homogeneously catalyzed chemical reactions. A myriad of novel complexes with different pincer arms have been synthetized and characterized, including a vast family of carbene pincers [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23], PNP [24][25][26][27][28][29], PNN [30,31], POP [32], PCP [33][34][35][36][37][38], SNS [39,40], NCN [41], NSiN [42], CNC [43], CNN [44], NNN [45], as well as sulfur- [46][47][48], silicon- [49,50], selenium- [51,52], and boron-functionalized [53,…”

Section: Introductionmentioning

confidence: 99%

Recent Progress with Pincer Transition Metal Catalysts for Sustainability

2020

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Our planet urgently needs sustainable solutions to alleviate the anthropogenic global warming and climate change. Homogeneous catalysis has the potential to play a fundamental role in this process, providing novel, efficient, and at the same time eco-friendly routes for both chemicals and energy production. In particular, pincer-type ligation shows promising properties in terms of long-term stability and selectivity, as well as allowing for mild reaction conditions and low catalyst loading. Indeed, pincer complexes have been applied to a plethora of sustainable chemical processes, such as hydrogen release, CO2 capture and conversion, N2 fixation, and biomass valorization for the synthesis of high-value chemicals and fuels. In this work, we show the main advances of the last five years in the use of pincer transition metal complexes in key catalytic processes aiming for a more sustainable chemical and energy production.

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“…Thioamides are highly attractive molecules in pharmaceuticals, agrochemicals, electronic chemicals, and materials sciences [ 17 – 27 ]. In coordination chemistry, pincer-type ligands containing a thioamide motif were shown to exhibit incomparable chelating ability towards selected transition metals, and the corresponding complexes were applied in various areas such as chemical-sensor materials, tunable redox-potential complexes, polymer hybrid luminescence materials, building blocks for multinuclear complexes, and as catalysts for cross-coupling reactions [ 28 – 35 ]. The thio-substitution of amides with LR is an efficient and straightforward method, because the amide substrates and LR are readily available and the reactions are easily operated [ 8 – 9 36 – 40 ].…”

Section: Introductionmentioning

confidence: 99%

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

Ling

Ding

et al. 2021

Beilstein J. Org. Chem.

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After completing the thio-substitution with Lawesson’s reagent, ethanol was found to be effective in the decomposition of the inherent stoichiometric six-membered-ring byproduct from the Lawesson’s reagent to a highly polarized diethyl thiophosphonate. The treatment significantly simplified the following chromatography purification of the desired thioamide in a small scale preparation. As scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not generate P-containing aqueous waste, and only organic effluents were discharged. It is believed that the optimized procedure offers the great opportunity of applying the Lawesson’s reagent for various thio-substitution reactions on a large scale.

show abstract

Secondary Thioamides as Multidentate Ligands for Functional Metal Complexes

Cited by 24 publications

References 74 publications

A Column-Free and Aqueous Waste-Free Process for Thioamide Preparation with Lawesson’s reagent

A Column-Free and Aqueous Waste-Free Process for Thioamide Preparation with Lawesson’s reagent

Recent Progress with Pincer Transition Metal Catalysts for Sustainability

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

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