Ionic and Organometallic‐Catalyzed Organosilane Reductions

Larson, Gerald L.; Fry, James L.

doi:10.1002/9780470572689

Cited by 44 publications

(49 citation statements)

References 704 publications

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“…[16] To promote the reactivities of the cerium salts further, we chose nitromethane as solvent. [17] Out of a range of different ceriumA C H T U N G T R E N N U N G (III) salts, ceriumA C H T U N G T R E N N U N G (III) perchlorate hexahydrate [18] (5 mol %) catalysed the reductive etherification of benzaldehyde (1) to dibenzyl ether (2) with triethylsilane in short reaction times and high yields ( Table 1, entry 4). Interestingly, ceriumA C H T U N G T R E N N U N G (III) triflate [19] was less efficient (Table 1, entry 2), whereas CeCl 3 [20] showed only very low activity (Table 1, entry 3).…”

Section: Resultsmentioning

confidence: 99%

“…The selective formation of 49 (Table 4, entry 7) is noteworthy, because esters are prone to reduction under hydrosilylation conditions. [2] The benzamide 51 (Table 4, entry 9), however, was only obtained in a low yield, even after a prolonged reaction time. Later we were able to show that tosyl-protected amides were tolerated much better under the given reaction conditions (vide infra).…”

Section: Wwwchemeurjorgmentioning

confidence: 97%

“…[1] However, the combination of reduction and subsequent coupling with a nucleophile allows for the synthesis of a variety of functionalized compounds directly from carbonyl compounds in a one-step procedure (Scheme 1). [2] The most prominent example of direct carbonyl compound transformations of this kind is reductive etherification, but this has found only limited applications in, for example, the synthesis of natural products. [3] This methodology circumvents major problems of classical etherification methods such as the Williamson ether synthesis (the formation of side products through elimination and high amounts of waste, for example).…”

Section: Introductionmentioning

confidence: 99%

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Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Gellert

Kahlcke

Feurer

et al. 2011

Chemistry A European J

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Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol%) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Gellert

Kahlcke

Feurer

et al. 2011

Chemistry A European J

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“…[69] This chemical can be prepared in atwo-step pathway by the reduction of 2-acetylfuran, which in turn can be derived from the platform chemical furan through aF riedel-Crafts acylation using cheap and highly accessible acetic anhydride (Scheme 20). [353,354] Recently, ag reen approach based on efficient and recyclable rare earth catalysts [e.g.S c(OTf) 3 ]h as been investigated for the Friedel-Crafts acylation of furan to 2-acetylfuran under microwave heating. [355] Interestingly,t his system affords 2-acetylfuran in an excellent yield of 99 %.…”

Section: -Ethyltetrahydrofuran (2-ethf)mentioning

confidence: 99%

“…Thes econd step comprises the reduction of 2-acetylfuran (using silanes as reducing agents) to 2-ETHF in up to 80 %y ield. [354] 2-n-Butyltetrahydrofuran (2-BTHF) 2-BTHF is aC 8 molecule bearing the THF moiety (boiling point = 160 8 8C; density = 0.86 gcm À3 )and represents apotential fuel additive. [69,317] Thesynthesis of 2-BTHF starting from the platform chemical furfural has been previously reported.…”

Section: -Ethyltetrahydrofuran (2-ethf)mentioning

confidence: 99%

Advanced Biofuels and Beyond: Chemistry Solutions for Propulsion and Production

et al. 2017

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Sustainably produced biofuels, especially when they are derived from lignocellulosic biomass, are being discussed intensively for future ground transportation. Traditionally, research activities focus on the synthesis process, while leaving their combustion properties to be evaluated by a different community. This Review adopts an integrative view of engine combustion and fuel synthesis, focusing on chemical aspects as the common denominator. It will be demonstrated that a fundamental understanding of the combustion process can be instrumental to derive design criteria for the molecular structure of fuel candidates, which can then be targets for the analysis of synthetic pathways and the development of catalytic production routes. With such an integrative approach to fuel design, it will be possible to improve systematically the entire system, spanning biomass feedstock, conversion process, fuel, engine, and pollutants with a view to improve the carbon footprint, increase efficiency, and reduce emissions.

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Iron‐promoted Reduction Reactions

Nagashima

Sunada

Noji

et al. 2014

Patai's Chemistry of Functional Groups

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Iron‐promoted reduction reactions are described from the standpoint of the catalyst design. Catalysis of three well‐defined precatalysts is the first topic; iron complexes having PNNP ligands, Shvo‐type complexes, and pincer compounds are active towards catalytic hydrogenation and transfer hydrogenation of ketones. The reduction mechanisms are in line with the concept of Noyori's metal‐ligand bifunctional catalysis, in which the ligand plays a key role in the hydrogenation of the carbonyl function. The redox‐active ligands in iron‐catalyzed hydrogenation and hydrosilylation of alkenes and alkynes provide other important aspects contributing to the catalyst design. In particular, redox properties of bis(imino)pyridine ligands assist the activation of H–H and H–Si bonds in molecular hydrogen and organohydrosilanes leading to efficient hydrogenation and hydrosilylation of alkenes. Reduction reactions mediated by iron compounds, which include catalytic hydrogenation, transfer hydrogenation, and hydrosilylation, are overviewed from organic synthesis, which is promoted by a mixture of iron salts and ligands, ill‐defined catalyst precursors, and nanoparticles. From these, the possible catalyst design of iron is discussed.

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Ionic and Organometallic‐Catalyzed Organosilane Reductions

Cited by 44 publications

References 704 publications

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Advanced Biofuels and Beyond: Chemistry Solutions for Propulsion and Production

Iron‐promoted Reduction Reactions

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