Synthesis of (η6-arene)(η5-cyclopentadienyl) iron (II) complexes with heteroatom and carbonyl substituents. Part I: Oxygen and carbonyl substituents

Roberts, R.M.G.

doi:10.1016/j.jorganchem.2005.12.070

Cited by 10 publications

(4 citation statements)

References 21 publications

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“…Such a method was also employed for the one-pot synthesis of a N-arylated amino acid. Other miscellaneous reactions were reported in the same papers [108,109].…”

Section: Late Transition Elements Of Groups 8-12 41 Ironsupporting

confidence: 56%

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irradiation in the preparation of transition metal complexes and organometallic compounds and also includes new, unpublished results.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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“…Such a method was also employed for the one-pot synthesis of a N-arylated amino acid. Other miscellaneous reactions were reported in the same papers [108,109].…”

Section: Late Transition Elements Of Groups 8-12 41 Ironsupporting

confidence: 56%

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

Gabano

Ravera

2022

Molecules

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“…[30] Althought he yield is rather modest (43%) it is superior to that obtained using SnCl 2 under strongly acidic conditions.A ni nteresting process hasb een observed in the nitro to carbonylc onversion of nitro esters 37, obtained by conjugate addition of ethyln itroacetate to chalcone derivatives 36 (Scheme12). [31] Upon treatment of nitro esters 37 with hydrogen peroxide in the presence of K 2 CO 3 ac oncomitant decarboxylation of the intermediate a-keto ester occurred with isolation of 5-keto acids 38.D FT-basedc alculationsh aved emonstrated that this process hasalow energy barrier and is highly exothermic.Asubsequent reactiono f keto acids 38 with amines or ammonium acetate under microwavei rradiation at 150 Wr eadilyp rovided unsaturated g-lactams 39 in satisfactory yields.…”

Section: O Xidative Methodsmentioning

confidence: 88%

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

2015

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This review article reports new procedures and practical application of the nitro to carbonyl conversion that appeared in the literature after our\ud comprehensive report published in 2004. Beside traditional and well explored reactant systems, new procedures including the utilization of molecular oxygen and photoredox catalysis have been introduced for the Nef reaction. Of notable interest is the utilizationof the nitro to carbonyl conversion in tandem and cascade processes aimed at the preparation of hetero and carbocyclic derivatives

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“…In the same year, Roberts reported the use of microwave heating conditions to introduce oxygen substituents into iron complex 205. 164 Ligand exchange reactions (Scheme 55) performed on ferrocene with phenolic reactants using microwave irradiation resulted in the isolation of [Fe(Cp)-(ArOH)] complexes in very low yields, probably because of the strong complexation or reaction with AlCl 3 that suppressed its Lewis acidity. Better results were obtained with phenyl-tbutylether and O-trimethylsilylphenol, resulting in the corresponding [Fe(Cp)(PhOH)] complex in 45% and 44% yield, respectively.…”

Section: Microwave Proceduresmentioning

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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Synthesis of (η6-arene)(η5-cyclopentadienyl) iron (II) complexes with heteroatom and carbonyl substituents. Part I: Oxygen and carbonyl substituents

Cited by 10 publications

References 21 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?

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

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