Why we might be misusing process mass intensity (PMI) and a methodology to apply it effectively as a discovery level metric

Monteith, Edward R.; Mampuys, Pieter; Summerton, Louise; Clark, James H.; Maes, Bert U. W.; McElroy, Con Robert

doi:10.1039/c9gc01537j

Cited by 86 publications

(61 citation statements)

References 38 publications

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“…The same conclusions, revealed from simulations of other reaction types (amide synthesis, Mitsunobu reaction), support the general applicability of these guidelines beyond thiosulfonate synthesis …”

Section: Assessing the Green Credentialssupporting

confidence: 72%

Thiosulfonates as Emerging Reactants: Synthesis and Applications

et al. 2019

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The synthetic strategies towards thiosulfonates (RSO2SR1) are comprehensively reviewed from their original discovery to recent advances. Incorporation of the green credentials of the synthetic procedures towards thiosulfonates allows one to judge the merits of the state of the art, beyond the typical yield of a product and availability of the reactants. As reactant for organic transformations, thiosulfonates are particularly interesting given their possibility to react with nucleophiles, electrophiles and radicals. This review aims to give researchers, not familiar with the field, a good understanding of the general applications of thiosulfonates, while not skipping the recent important advances. The related, but less explored, selenosulfonates (RSO2SeR1) are also covered.

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Section: Assessing the Green Credentialssupporting

confidence: 72%

Thiosulfonates as Emerging Reactants: Synthesis and Applications

et al. 2019

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“…Nowadays, transformations are evaluated numerically using parameters such as atom economy , E factor , process mass intensity , and many others. 6 − 17 More recently, enormous efforts have been made to develop the science of “lifecycle assessment”—the quantitative metrics by which the total mass and energy inputs and waste outputs of a given chemical transformation are evaluated for their environmental impact. 18 − 21 Since then, industrial chemists have led the charge by compiling important guides on reagent and solvent selection.…”

Section: Introductionmentioning

confidence: 99%

C–H Activation: Toward Sustainability and Applications

2021

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Since the definition of the “12 Principles of Green Chemistry” more than 20 years ago, chemists have become increasingly mindful of the need to conserve natural resources and protect the environment through the judicious choice of synthetic routes and materials. The direct activation and functionalization of C–H bonds, bypassing intermediate functional group installation is, in abstracto , step and atom economic, but numerous factors still hinder the sustainability of large-scale applications. In this Outlook, we highlight the research areas seeking to overcome the sustainability challenges of C–H activation: the pursuit of abundant metal catalysts, the avoidance of static directing groups, the replacement of metal oxidants, and the introduction of bioderived solvents. We close by examining the progress made in the subfield of aryl C–H borylation from its origins, through highly efficient but precious Ir-based systems, to emerging 3d metal catalysts. The future growth of this field will depend on industrial uptake, and thus we urge researchers to strive toward sustainable C–H activation.

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“…Under the standard flow conditions shown in Table 2, the desired product 2 was constantly obtained in 91–94% yields. No deactivation was observed after continuous reaction for 120 h. The overall reaction economy was assessed by evaluating the process mass intensity (PMI), [11] which confirmed the advantages of using heterogeneous catalysts; the trifluoroethanol solvent could also be reused in the flow system (Table 2). Indeed, recycling experiments, carried out using recovered trifluoroethanol and reusing the catalyst‐packed reactor with the same contents, confirmed that consistently high yields were achieved for four runs.…”

Section: Methodsmentioning

confidence: 73%

Sequential Continuous‐Flow Synthesis of 3‐Aryl Benzofuranones

Xin

Rao

Ishitani

et al. 2021

Chemistry An Asian Journal

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A sequential continuous-flow system to produce 3-aryl benzofuranones was developed. Starting from 2,4-ditert-butylphenol and glyoxylic acid monohydrate, both the initial cyclocondensation and the subsequent FriedelÀ Crafts alkylation were catalyzed by the same heterogeneous catalyst, Amberlyst-15H. The catalyst has a promising lifetime for these two steps, and it was able to be recovered and reused for several runs without deactivation. By using the established flow system, 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-3H-benzofuran-2-one (Irganox HP-136), which is a commercial antioxidant, was prepared in 88% two-step yield. Reactions with various aromatic compounds proceeded well under flow conditions to afford 3-aryl benzofuranone derivatives in high yields with good functional group compatibility.

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Why we might be misusing process mass intensity (PMI) and a methodology to apply it effectively as a discovery level metric

Abstract: Are the comparisons of PMI values fair and informative, are you making a like versus like assessment?

Cited by 86 publications

References 38 publications

Thiosulfonates as Emerging Reactants: Synthesis and Applications

Thiosulfonates as Emerging Reactants: Synthesis and Applications

C–H Activation: Toward Sustainability and Applications

Sequential Continuous‐Flow Synthesis of 3‐Aryl Benzofuranones

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