Microwave Assisted Synthesis of Molybdenum and Tungsten Tetracarbonyl Complexes with a Pyrazolylpyridine Ligand. Crystal structure of cis-[Mo(CO)4{ethyl[3-(2-pyridyl)-1-pyrazolyl]acetate}]

Coelho, Ana C.; Paz, Filipe A. A.; Klinowski, Jacek; Pillinger, Martyn; Gonçalves, Isabel S.

doi:10.3390/molecules11120940

Cited by 10 publications

(10 citation statements)

References 59 publications

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“…Molybdenum complex 118 (Scheme ) and cis -[W(CO) 4 (pzpy)] 119 (Scheme ) were synthesized under microwave irradiation from ligand 116 with [Mo(CO) 6 ] and [W(CO) 6 ] , respectively. Tungsten complex 119 was obtained after 15 min irradiation, with longer reaction times required compared to that of molybdenum complex 118 due to the lower reactivity of [W(CO) 6 ] compared to [Mo(CO) 6 ] (15 min instead of 30 s) …”

Section: Groupmentioning

confidence: 91%

“…cis -[Mo(CO) 4 (piperidine) 2 ] 117 and cis -[Mo(CO) 4 (pzpy)] 118 (pzpy = ethyl[3-(2-pyridyl)-1-pyrazolyl]acetate) were synthesized by reacting [Mo(CO) 6 ] under microwave irradiation with piperidine and pzpy 116 , respectively (Scheme , reactions A, B, and C). Complexes were recovered in shorter reaction times and in higher yields than when obtained by synthesis in solution.…”

Section: Groupmentioning

confidence: 99%

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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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Section: Groupmentioning

confidence: 91%

Section: Groupmentioning

confidence: 99%

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

et al. 2019

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“…For related structures with 2-(3-pyrazolyl)pyridine or its derivatives, see: Coelho et al (2006Coelho et al ( , 2007; Fleming et al (1998); Jones et al (1997); Lam et al (1997); Leita et al (2004); Li (2007); Liu et al (2006); Mokuolu et al (2007); ; Hu, Wang et al (2006); Hu et al (2008); Huo et al (2006); Ward, Fleming et al (1998); Ward, Mann et al (1998). For detailed background to the role of hydrogen bonds in the supramolecular organization of organic crystals, see: Nangia & Desiraju (1998).…”

Section: Related Literaturementioning

confidence: 99%

“…Our research group has been particularly interested in the use of this molecule and its derivatives. For example, we have reported the crystal structures of both the molybdenum complex cis-[Mo(CO) 4 L] (Coelho et al, 2006) and the organic ligand L {ethyl[3-(2-pyridyl)-1-pyrazolyl]acetate} (Coelho et al, 2007). We have recently isolated single crystals of (I) as a secondary (minor) phase (see Experimental).…”

Section: S1 Commentmentioning

confidence: 99%

2-(1H-Pyrazol-3-yl)pyridinium chloride monohydrate

2009

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The title organic salt, C8H8N3 +·Cl−·H2O, exhibits a rich hydrogen-bonding network involving all constituent species. The water molecules are engaged in strong O—H⋯Cl interactions with the chloride anions, two neighboring protonated 2-(1H-pyrazol-3-yl)pyridinium species interact via N—H⋯N bonds with two pyrazole rings. Further, a short and highly directional C—H⋯O interaction is observed connecting the pyridinium ring to the water molecule of crystallization. Weak C—H⋯Cl and N—H⋯Cl interactions contribute to the stabilization of the crystal structure.

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“…Our research group has been particularly interested in its excellent N,N-chelating properties. For example, its coordination complexes with molybdenum and europium lead to chemical systems exhibiting interesting catalytic (Coelho et al, 2006;Bruno, Pereira et al, 2007;Bruno, Fernandes et al, 2006;Gago et al, 2006) and photophysical properties (Gago et al, 2005), respectively. Here, we report the crystal structure of the monohydrate of this organic compound, (I), determined at 100 (2) K.…”

Section: Commentmentioning

confidence: 99%