2014
DOI: 10.1002/cssc.201402477
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Phosphorus‐based Bifunctional Organocatalysts for the Addition of Carbon Dioxide and Epoxides

Abstract: Bifunctional phosphonium salts were synthesized and employed as organocatalysts for the atom efficient synthesis of cyclic carbonates from CO2 and epoxides for the first time. These catalysts were obtained in high yields by a modular, straightforward one-step synthesis. The hydrogen-bond donating alcohol function in the side chain leads to a synergistic effect accelerating the catalytic reaction. The desired cyclic carbonates are obtained in high yields and selectivity under solvent-free reaction conditions wi… Show more

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Cited by 125 publications
(67 citation statements)
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“…Under optimized reaction conditions (130 °C, 25 bar, 3 h) a yield of 97 % PC was achieved, but no recycling experiments were presented. Werner and Büttner used simple bifunctional hydroxyl‐phosphonium salt catalysts 72. Under solvent‐free conditions and without any cocatalyst, quantitative PC yields were achieved with 2 mol % of catalyst at 90 °C under 10 bar of CO 2 after 3 h. However, the catalyst decomposed during recycling and could be only reused five times with loss in activity.…”
Section: Phosphonium Salts As Catalystsmentioning
confidence: 99%
See 1 more Smart Citation
“…Under optimized reaction conditions (130 °C, 25 bar, 3 h) a yield of 97 % PC was achieved, but no recycling experiments were presented. Werner and Büttner used simple bifunctional hydroxyl‐phosphonium salt catalysts 72. Under solvent‐free conditions and without any cocatalyst, quantitative PC yields were achieved with 2 mol % of catalyst at 90 °C under 10 bar of CO 2 after 3 h. However, the catalyst decomposed during recycling and could be only reused five times with loss in activity.…”
Section: Phosphonium Salts As Catalystsmentioning
confidence: 99%
“…In particular, phosphonium salts exhibit higher activity and stability of catalysts. However, there are only a few examples with reaction conditions of <100 °C and <20 bar of CO 2 , and again, to separate PC from the molecular catalyst, highly energy demanding distillation of the cyclic carbonate is necessary 72. 81 Thus, a way for more efficient epoxide/CO 2 activation has to be found to enable the synthesis of PC at room temperature and atmospheric CO 2 pressure.…”
Section: Phosphonium Salts As Catalystsmentioning
confidence: 99%
“…[1][2][3][4] A frequently studied reaction is the cycloaddition of carbon dioxide to epoxides. [11][12][13] Frequently employed catalytic systems are based on Lewis acidic metal complexes, [14][15][16] alkali metal halides 17,18 as well as imidazolium, 19-21 phosphonium [22][23][24][25][26] or ammonium salts. the synthesis from diols and phosgene.…”
Section: Introductionmentioning
confidence: 99%
“…46,47 The groups of North, Endo and Lu reported the use of metal complex catalysts based on aluminum and titanium usually in combination with ammonium salts as cocatalysts. 26,32,[53][54][55][56][57] Most recently we turned our attention to the conversion of carbon disulfide in this reaction. [46][47][48][49][50][51][52] We are interested in the utilization of carbon dioxide as a C1 building block and developed one-and two component catalytic systems for the synthesis of cyclic carbonates from carbon dioxide and epoxides.…”
Section: Introductionmentioning
confidence: 99%
“…Bifunctional salts 1a and 1b showed much higher activity under these conditions, yielding 3 in 97 and 92%, respectively (entries 3 and 4). 26,27 Further experiments were carried out with 1a …”
Section: ■ Results and Discussionmentioning
confidence: 99%