Mechanochemical Palladium‐Catalyzed Carbonylative Reactions Using Mo(CO)<sub>6</sub>

Bonn, Pit van; Bolm, Carsten; Hernández, José G.

doi:10.1002/chem.201904528

Cited by 26 publications

(15 citation statements)

References 62 publications

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“…a) Setup for synchrotron X‐ray powder diffraction, Raman spectroscopy, and real‐time temperature sensing [208] . b) Milling jar for pressure and temperature sensing [210] . c) Modified milling vial for online nondispersive infrared spectroscopy monitoring.…”

Section: Mechanochemistry and The Twelve Principles Of Green Chemistrymentioning

confidence: 99%

“…Other strategies to follow mechanochemical reactions include manometric real‐time monitoring to study reaction mechanisms in the mechanosynthesis of zeolitic imidazolate frameworks, [24] palladium‐catalyzed carbonylative reactions, [210] and cyclodehydrogenation reactions [211] . Complementarily, formation of volatile products in ball milling reactions has been monitored by gas chromatography (Scheme 10), [168] while online spectroscopic identification of gaseous products generated by ball milling has been achieved by nondispersive infrared spectroscopy [212,213] .…”

Section: Mechanochemistry and The Twelve Principles Of Green Chemistrymentioning

confidence: 99%

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Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

2021

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In recent years, mechanochemistry has been growing into a widely accepted alternative for chemical synthesis. In addition to their efficiency and practicality, mechanochemical reactions are also recognized for their sustainability. The association between mechanochemistry and Green Chemistry often originates from the solvent-free nature of most mechanochemical protocols, which can reduce waste production. However, mechanochemistry satisfies more than one of the Principles of Green Chemistry. In this Review we will present a series of examples that will clearly illustrate how mechanochemistry can significantly contribute to the fulfillment of Green Chemistry in a more holistic manner.

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Section: Mechanochemistry and The Twelve Principles Of Green Chemistrymentioning

confidence: 99%

Section: Mechanochemistry and The Twelve Principles Of Green Chemistrymentioning

confidence: 99%

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

2021

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“…The use of pressure as a handle for monitoring reaction progress provided early examples of multistep mechanochemical processes in the context of inorganic chemistry, 35 but stipulates the participation of gaseous reactants or products. 36 Our team recently demonstrated how using a carbonate reactant permits direct monitoring of the mechanochemical synthesis of MOFs through pressure increase resulting from CO 2 release (Figure 2). 37…”

Section: Pressure Monitoringmentioning

confidence: 99%

Toward Mechanistic Understanding of Mechanochemical Reactions Using Real-Time In Situ Monitoring

et al. 2022

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Conspectus The past two decades have witnessed a rapid emergence of interest in mechanochemistry–chemical and materials reactivity achieved or sustained by the action of mechanical force–which has led to application of mechanochemistry to almost all areas of modern chemical and materials synthesis: from organic, inorganic, and organometallic chemistry to enzymatic reactions, formation of metal–organic frameworks, hybrid perovskites, and nanoparticle-based materials. The recent success of mechanochemistry by ball milling has also raised questions about the underlying mechanisms and has led to the realization that the rational development and effective harnessing of mechanochemical reactivity for cleaner and more efficient chemical manufacturing will critically depend on establishing a mechanistic understanding of these reactions. Despite their long history, the development of such a knowledge framework for mechanochemical reactions is still incomplete. This is in part due to the, until recently, unsurmountable challenge of directly observing transformations taking place in a rapidly oscillating or rotating milling vessel, with the sample being under the continuous impact of milling media. A transformative change in mechanistic studies of milling reactions was recently introduced through the first two methodologies for real-time in situ monitoring based on synchrotron powder X-ray diffraction and Raman spectroscopy. Introduced in 2013 and 2014, the two new techniques have inspired a period of tremendous method development, resulting also in new techniques for mechanistic mechanochemical studies that are based on temperature and/or pressure monitoring, extended X-ray fine structure (EXAFS), and, latest, nuclear magnetic resonance (NMR) spectroscopy. The new technologies available for real-time monitoring have now inspired the development of experimental strategies and advanced data analysis approaches for the identification and quantification of short-lived reaction intermediates, the development of new mechanistic models, as well as the emergence of more complex monitoring methodologies based on two or three simultaneous monitoring approaches. The use of these new opportunities has, in less than a decade, enabled the first real-time observations of mechanochemical reaction kinetics and the first studies of how the presence of additives, or other means of modifying the mechanochemical reaction, influence reaction rates and pathways. These studies have revealed multistep reaction mechanisms, enabled the identification of autocatalysis, as well as identified molecules and materials that have previously not been known or have even been considered not possible to synthesize through conventional approaches. Mechanistic studies through in situ powder X-ray diffraction (PXRD) and Raman spectroscopy have highlighted the formation of supramolecular complexes (for example, cocrystals) as critical intermediates in organic and metal–organic synthesis and have also been combined with isotope labeling strategies to provide a deep...

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“…Ball milling, which features environmentally friendly and solvent-less synthesis, has emerged as a powerful mechanochemical technique in synthetic chemistry in the past few years. − In particular, several practical examples of mechanochemically transition-metal catalyzed C–H bond functionalization have been developed since the pioneering work by Cúric and co-workers. − For instance, Bolm and co-workers reported the first catalytic example of Rh-catalyzed C–H bond functionalization using a ball mill . Other groups such as Ito’s group and Su’s group also contributed several elegant C–H bond transformations of diverse substrates. , Our group has a continuous interest in developing green synthetic approaches that merge C–H bond functionalization with ball milling.…”

Section: Introductionmentioning

confidence: 99%

Solvent-less Dehydrogenative C–H Etherification with Alcohols Using Mechanochemistry

Zhou

Hao

Mao

et al. 2021

ACS Sustainable Chem. Eng.

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The aromatic C–H bond etherification with alcohols is one of the most atom-efficient ways to construct aryl ethers. However, it often requires a large excess of alcohols as etherification reagents, which limits the substrate scope (especially for the valuable alcohols). Herein, an alternative mechanochemical C–H bond etherification of oximes with diverse primary and secondary alcohols was developed for the first time. Given the solvent-less condition of ball milling technique, the amount of alcohols used in this chemistry has been significantly reduced (1.5–3.0 equiv to the substrates), thus enabling the incorporation of a wide range of alcohols in the C–H bond etherification for the first time. The present mechanochemical protocol enhances the application prospect of the cross dehydrogenative C–H etherification strategy in the late-stage synthesis of complex aromatic ethers.

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Mechanochemical Palladium‐Catalyzed Carbonylative Reactions Using Mo(CO)₆

Cited by 26 publications

References 62 publications

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

Toward Mechanistic Understanding of Mechanochemical Reactions Using Real-Time In Situ Monitoring

Solvent-less Dehydrogenative C–H Etherification with Alcohols Using Mechanochemistry

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Mechanochemical Palladium‐Catalyzed Carbonylative Reactions Using Mo(CO)6

Cited by 26 publications

References 62 publications

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

Toward Mechanistic Understanding of Mechanochemical Reactions Using Real-Time In Situ Monitoring

Solvent-less Dehydrogenative C–H Etherification with Alcohols Using Mechanochemistry

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Mechanochemical Palladium‐Catalyzed Carbonylative Reactions Using Mo(CO)₆