Development of a solvent selection guide for aldehyde-based direct reductive amination processes

McGonagle, Fiona I.; Macmillan, Donna S.; Murray, Jane; Sneddon, Helen F.; Jamieson, Craig; Watson, Allan J. B.

doi:10.1039/c3gc40359a

Cited by 63 publications

(57 citation statements)

References 56 publications

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“…Reaction specific solvent selection guides are now available [87][88][89], which rank a set of solvents according to the observed performance (not greenness). The requirement of the solvent in chromatography as the mobile phase is so obvious in its importance that solvent guides for this application predate all other tools [90,91], and has now been revived as a research topic [92,93].…”

Section: Discussionmentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,067

737

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Driven by legislation and evolving attitudes towards environmental issues, establishing green solvents for extractions, separations, formulations and reaction chemistry has become an increasingly important area of research. Several general purpose solvent selection guides have now been published with the aim to reduce use of the most hazardous solvents. This review serves the purpose of explaining the role of these guides, highlighting their similarities and differences. How they can be used most effectively to enhance the greenness of chemical processes, particularly in laboratory organic synthesis and the pharmaceutical industry, is addressed in detail.

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Section: Discussionmentioning

confidence: 99%

Tools and techniques for solvent selection: green solvent selection guides

Byrne

Jin

Paggiola

et al. 2016

Sustain Chem Process

1,067

737

View full text Add to dashboard Cite

show abstract

“…However, these two sets of criteria are mostly treated separately. Another way that has been used to take into account the role that the solvent plays is to restrict the guide to a particular application or to target the elimination of a particular solvent, such as CH 2 Cl 2 in chromatography [ 82 , 83 ], amide coupling [ 84 ], reductive amination [ 85 ] and olefin metathesis reactions [ 86 ].…”

Section: ‘Green’ Solventsmentioning

confidence: 99%

Solvents and sustainable chemistry

2015

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Solvents are widely recognized to be of great environmental concern. The reduction of their use is one of the most important aims of green chemistry. In addition to this, the appropriate selection of solvent for a process can greatly improve the sustainability of a chemical production process. There has also been extensive research into the application of so-called green solvents, such as ionic liquids and supercritical fluids. However, most examples of solvent technologies that give improved sustainability come from the application of well-established solvents. It is also apparent that the successful implementation of environmentally sustainable processes must be accompanied by improvements in commercial performance.

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“…Cyrene has previously demonstrated successful application in materials chemistry, 41,42 in addition to synthetic organic transformations. [43][44][45] Based on our interest in solvent replacement strategies, 21,[46][47][48][49] we are pleased to report the use of Cyrene as a bio-based solvent in amide bond formation.…”

Section: -40mentioning

confidence: 99%

Cyrene as a bio-based solvent for HATU mediated amide coupling

et al. 2018

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Amide bonds are one of the underpinning linkages in all living systems and are fundamental within drug discovery. Current methods towards their synthesis frequently rely on the use of dipolar aprotic solvents; however, due to increasingly stringent regulations and growing societal pressures, safe and more sustainable alternatives are highly sought after. Herein, we evaluate the application of the bio-based solvent Cyrene™ in the HATU mediated synthesis of amides and peptides. We found that Cyrene functioned as a competent replacement for DMF in the synthesis of a series of lead-like compounds and dipeptides (25 examples, 63-100%).

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Development of a solvent selection guide for aldehyde-based direct reductive amination processes

Cited by 63 publications

References 56 publications

Tools and techniques for solvent selection: green solvent selection guides

Tools and techniques for solvent selection: green solvent selection guides

Solvents and sustainable chemistry

Cyrene as a bio-based solvent for HATU mediated amide coupling

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