Preparation of organometallic uracil-analogue Fischer carbene complexes: Comparative study of conventional heating vs microwave irradiation

Artillo, Antonietta; Sala, Giorgio Della; Santis, Marco De; Llordés, Anna; Ricart, Susagna; Spinella, Aldo

doi:10.1016/j.jorganchem.2006.08.097

Cited by 19 publications

(6 citation statements)

References 11 publications

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“…In general, thermal reactions required reaction times >30 min depending on the reagents, whereas MWs (400 W) required 30 min or less. The yields under MW irradiation were similar with respect to the thermal ones [81].…”

Section: Chromium Molybdenum and Tungstensupporting

confidence: 65%

Microwave-Assisted Synthesis: Can Transition Metal Complexes Take Advantage of This “Green” Method?

Gabano

Ravera

2022

Molecules

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Microwave-assisted synthesis is considered environmental-friendly and, therefore, in agreement with the principles of green chemistry. This form of energy has been employed extensively and successfully in organic synthesis also in the case of metal-catalyzed synthetic procedures. However, it has been less widely exploited in the synthesis of metal complexes. As microwave irradiation has been proving its utility as both a time-saving procedure and an alternative way to carry on tricky transformations, its use can help inorganic chemists, too. This review focuses on the use of microwave irradiation in the preparation of transition metal complexes and organometallic compounds and also includes new, unpublished results. The syntheses of the compounds are described following the group of the periodic table to which the contained metal belongs. A general overview of the results from over 150 papers points out that microwaves can be a useful synthetic tool for inorganic chemists, reducing dramatically the reaction times with respect to traditional heating. This is often accompanied by a more limited risk of decomposition of reagents or products by an increase in yield, purity, and (sometimes) selectivity. In any case, thermal control is operative, whereas nonthermal or specific microwave effects seem to be absent.

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Section: Chromium Molybdenum and Tungstensupporting

confidence: 65%

Microwave-Assisted Synthesis: Can Transition Metal Complexes Take Advantage of This “Green” Method?

Gabano

Ravera

2022

Molecules

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“…Although microwave irradiation is widely used today in organic synthesis, only a few papers report its exploitation in coordination chemistry. [34][35][36][37] In this study we have developed a convenient and efficient method with a closed microwave system, which allows the dramatic reduction of the reaction times for the different steps of synthesis of trinuclear Ru(II) dendrons based on the bridging ligands PHEHAT and TPAC. For example, the global reaction time needed to form the dichloro trinuclear complex can be shortened by 34 h while keeping similar yields.…”

Section: Discussionmentioning

confidence: 99%

Trinuclear ruthenium dendrons based on bridging PHEHAT and TPAC ligands

2011

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Novel polynuclear compounds, the trinuclear precursor complex cis-{[(phen)(2)Ru(PHEHAT)](2)Ru(CH(3)CN)(2)}(6+) 4 and the trinuclear TPAC (tetrapyrido[3,2-a:2',3'-c:3'',2'-h:2''',3'''-j]acridine) complex {[(phen)(2)Ru(PHEHAT)](2)Ru(TPAC)}(6+) 5 have been prepared. Their electrochemistry and photophysics indicate that the (3)MLCT (metal to ligand charge transfer) emissions involve the external {Ru(PHEHAT)} moieties for both complexes and there is no spectro-electrochemical correlation. The trinuclear dendron with the TPAC ligand represents a key compound for future constructions of much larger species thanks to the TPAC that could bridge another polynuclear precursor. For decreasing the length of preparation of these compounds, microwave assisted syntheses have been tested and used not only for the targeted complexes but also for the precursors ((phen)(2)RuCl(2), {(phen)(2)Ru(phendione)}(2+), {(phen)(2)Ru(PHEHAT)}(2+) (PHEHAT = 1,10-phenanthrolino[5,6-b]1,4,5,8,9,12-hexaazatriphenylene), (DMSO)(4)RuCl(2)), and for the bridging TPAC ligand itself. The microwave method allows a drastic decrease of the preparation times, especially in the case of the TPAC, from 8 days to 60 min.

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“…By using microwave irradiation, reaction time was considerably reduced from hours (at room temperature) to a few minutes (at 60 °C) (Scheme 27). 109 Despite this, yields were in the same range as conventional solution-based synthesis. Change of the acetylene moiety was studied: a trimethylsilylsubstituted alkynyl carbene complex was used, but low yields were obtained due to the easy desilylation of the starting material.…”

Section: Microwave Irradiation For the Synthesis Of Group 6 Metal Com...mentioning

confidence: 99%

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

et al. 2019

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Organometallic complexes: these two words jump to the mind of the chemist and are directly associated with their utility in catalysis or as a pharmaceutical. Nevertheless, to be able to use them, it is necessary to synthesize them, and it is not always a small matter. Typically, synthesis is via solution chemistry, using a roundbottom flask and a magnetic or mechanical stirrer. This review takes stock of alternative technologies currently available in laboratories that facilitate the synthesis of such complexes. We highlight five such technologies: mechanochemistry, also known as solvent-free chemistry, uses a mortar and pestle or a ball mill; microwave activation can drastically reduce reaction times; ultrasonic activation promotes chemical reactions because of cavitation phenomena; photochemistry, which uses light radiation to initiate reactions; and continuous flow chemistry, which is increasingly used to simplify scaleup. While facilitating the synthesis of organometallic compounds, these enabling technologies also allow access to compounds that cannot be obtained in any other way. This shows how the paradigm is changing and evolving toward new technologies, without necessarily abandoning the round-bottom flask. A bright future is ahead of the organometallic chemist, thanks to these novel technologies. CONTENTS1. Introduction 7530 2. Technologies 7530 2.1. Grinding and Milling 7530 2.2. Microwave Irradiation 7531 2.3. Ultrasound Activation 7531 2.4. Photochemistry 7532 2.5. Continuous Flow 7532 3. Contribution of Each Technology Compared to Classical Syntheses 7533 4. Lithium and Magnesium 7534 4.1. Mechanochemical Access to Grignard Reagents 7534 4.2. Microwave Irradiation for the Synthesis of Magnesium Complexes 7534 4.3. Ultrasonic Procedures 7535 4.4. Continuous Flow Syntheses 7535 5. Groups 2, 3, 4, and 5 7537 5.1. Mechanochemical Procedures for Complexes of Groups 2, 3, and 4 7537 5.2. Microwave Irradiation for the Synthesis of Vanadium Complexes 7537 5.3. Synthesis of Vanadium Complexes Using Ultrasound 7538 6. Group 6 7538 6.1. Mechanosynthesis of Molybdenum and Chromium Complexes 7538 6.2. Microwave Irradiation for the Synthesis of Group 6 Metal Complexes 7539 6.3. Photochemistry for Synthesis of Group 6 Metal Complexes 7543 6.4. Continuous Flow Chemistry for Synthesis of Chromium Complexes 7545 7. Group 7 7545 7.1. Mechanosynthesis of Rhenium Complexes 7545 7.2. Microwave Irradiation for the Synthesis of Group 7 Metal Complexes 7546 7.3. Photochemical Synthesis of Manganese and Rhenium Complexes 7549 8. Group 8 7550 8.1. Synthesis of Iron and Ruthenium Complexes Using Ball Milling 7550 8.2. Microwave Procedures 7552 8.3. Ultrasonic Irradiation for Iron Complexes 7562 8.4. Syntheses of Iron and Ruthenium Complexes Using Photochemistry 7563 8.5. Continuous Flow Conditions to Prepare Iron and Ruthenium Complexes 7566 9. Group 9 7566 9.1. Synthesis of Cobalt and Rhodium Complexes by Mechanochemistry 7566 9.2. Procedures Using Microwave Irradiation 7569 9.3. Photochemical Synthesis of Iridium Complexes 7...

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Preparation of organometallic uracil-analogue Fischer carbene complexes: Comparative study of conventional heating vs microwave irradiation

Cited by 19 publications

References 11 publications

Microwave-Assisted Synthesis: Can Transition Metal Complexes Take Advantage of This “Green” Method?

Microwave-Assisted Synthesis: Can Transition Metal Complexes Take Advantage of This “Green” Method?

Trinuclear ruthenium dendrons based on bridging PHEHAT and TPAC ligands

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

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