Baxendale GroupAdvanced synthetic chemistry, engineered for scaleDepartment of Chemistry

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Publications

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Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringAutomation and analyticsPhotochemistryHazardous and reactive intermediatesImmobilised reagents and scavengers

30 publications found for Hazardous and reactive intermediates

Cover of Molecules
Graphical abstract for Flow Hydrodediazotization of Aromatic Heterocycles

Journal article

Flow Hydrodediazotization of Aromatic Heterocycles

Röder, L.; Nicholls, A. J.; Baxendale, I. R.

Molecules · 2019 · 24(10) · 1996–1996(18)

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was …

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Cover of J. Org. Chem.
Graphical abstract for The Indium and Zinc Mediated Acyloxyallylation of Protected and Unprotected Aldotetroses - Revealing a Pronounced Diastereodivergence and a Fundamental Difference in the Performance of the Mediating Metal

Journal article

The Indium and Zinc Mediated Acyloxyallylation of Protected and Unprotected Aldotetroses - Revealing a Pronounced Diastereodivergence and a Fundamental Difference in the Performance of the Mediating Metal

Draskovits, M.; Stanetty, C.; Baxendale, I. R.; Mihovilovic, M. D.

J. Org. Chem. · 2018 · 83 · 2647–2659

Hazardous and reactive intermediates

The acyloxyallylation of unprotected aldoses was first demonstrated more than a decade ago as a potentially elegant two-carbon homologation of reducing sugars (upon ozonolysis), however, its application in real case syntheses remained scarce. Following up o…

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Cover of Euro. J. Org. Chem.
Graphical abstract for A Continuous Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of New Etomidate Derivatives

Journal article

A Continuous Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of New Etomidate Derivatives

Baumann, M.; Baxendale, I. R.

Euro. J. Org. Chem. · 2017 · 44 · 6518–6524

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

A simple yet robust flow set-up for the efficient desulfurization of a series of thioimidazoles is presented generating the corresponding imidazole derivatives in high yields. The strategic choice of peristaltic over piston pumps allowed reliable delivery of …

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Cover of Biorg. Med. Chem.
Graphical abstract for A continuous flow synthesis and derivatization of 1,2,4-thiadiazoles

Journal article

A continuous flow synthesis and derivatization of 1,2,4-thiadiazoles

Baumann, M.; Baxendale, I. R.

Biorg. Med. Chem. · 2017 · 25 · 6218–6223

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

A continuous flow process is presented that enables the efficient synthesis and derivatization of 1,2,4-thiadiazole heterocycles. Special attention was given to the safe handling of the versatile yet hazardous trichloromethane sulfenylchloride reagent includi…

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Cover of Molbank
Graphical abstract for Rac-20,3a,6,6,60,60-Hexamethyl-3a,3b,6,7-tetrahydrospiro-[ benzo[2,3]cyclopropa[1,2-c]pyrazole- 1,10-cyclo-hepta[2,4]diene]

Journal article

Rac-20,3a,6,6,60,60-Hexamethyl-3a,3b,6,7-tetrahydrospiro-[ benzo[2,3]cyclopropa[1,2-c]pyrazole- 1,10-cyclo-hepta[2,4]diene]

Baumann, M.; Lapraille, S.; Baxendale, I. R.

Molbank · 2017 · M948

Synthetic and heterocyclic chemistryHazardous and reactive intermediates

This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a tran…

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Cover of Molecules
Graphical abstract for Exploring Flow Procedures for Diazonium Formation

Journal article

Exploring Flow Procedures for Diazonium Formation

Hu, T.; Baxendale, I. R.; Baumann, M.

Molecules · 2016 · 21 · 918–941

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

The synthesis of diazonium salts is historically an important transformation extensively utilized in dye manufacture. However the highly reactive nature of the diazonium functionality has additionally led to the development of many new reactions including sev…

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Cover of Beilstein J. Org. Chem.
Graphical abstract for Flow carbonylation of sterically hindered ortho-substituted iodoarenes

Journal article

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

Mallia, C. J.; Walter, G. C.; Baxendale, I. R.

Beilstein J. Org. Chem. · 2016 · 12 · 1503–1511

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

The flow synthesis of ortho-substituted carboxylic acids, using carbon monoxide gas, has been studied for a number of substrates. The optimised conditions make use of a simple catalyst system compromising of triphenylphosphine as the ligand and palladium acet…

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Cover of J. Org. Chem.
Graphical abstract for Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade

Journal article

Batch and Flow Synthesis of Pyrrolo[1,2-a]-quinolines via an Allene-Based Reaction Cascade

Baumann, M.; Baxendale, I. R.

J. Org. Chem. · 2015 · 80 · 10806–10816

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

An efficient reaction cascade delivering a series of pyrrolo[1,2-a]quinolines bearing phosphonate or phosphine oxide moieties is presented. This sequence exploits the in situ transformation of propargylic alcohols into transient allenes by means of a strategi…

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Cover of Molecules
Graphical abstract for Synthesis of Riboflavines, Quinoxalinones and Benzodiazepines through Chemoselective Flow Based Hydrogenations

Journal article

Synthesis of Riboflavines, Quinoxalinones and Benzodiazepines through Chemoselective Flow Based Hydrogenations

Baumann M.; Baxendale, I. R.; Hornung, C. H.; Ley, S. V.; Rojo, M. V.; Roper, K. A.

Molecules · 2014 · 19 · 9736–9759

Synthetic and heterocyclic chemistryRoute design and process chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

Robust chemical routes towards valuable bioactive entities such as riboflavines, quinoxalinones and benzodiazepines are described. These make use of modern flow hydrogenation protocols enabling the chemoselective reduction of nitro group containing building b…

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Cover of Org. Process Res. Dev.
Graphical abstract for A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid

Journal article

A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid

Battilocchio, C.; Baxendale, I. R.; Biava, M.; Kitching, M. O.; Ley, S. V.

Org. Process Res. Dev. · 2012 · 16 · 798–810

Synthetic and heterocyclic chemistryFlow chemistry and reaction engineeringHazardous and reactive intermediates

The development of a new, high-yielding, scalable and safe process for the preparation of 2-aminoadamantane-2-carboxylic acid (1) is described. This geminal, functionalized achiral amino acid has been reported to possess interesting biological activity as a t…

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Cover of Rapid Commun. Mass Spectrom.
Graphical abstract for Continuous flow reaction monitoring using an on-line miniature mass spectrometer

Journal article

Continuous flow reaction monitoring using an on-line miniature mass spectrometer

Browne, D. L.; Wright, S.; Deadman, B.; Dunnage, S.; Baxendale, I. R.; Turner, R.; Ley, S. V.

Rapid Commun. Mass Spectrom. · 2012 · 26 · 1999–2010

Flow chemistry and reaction engineeringAutomation and analyticsHazardous and reactive intermediates

A recently developed miniature electrospray ionisation mass spectrometer has been coupled to a preparative flow chemistry system in order to monitor reactive intermediates and competing reaction paths, screen starting materials, and optimise reaction conditio…

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Cover of Org. Biomol. Chem.
Graphical abstract for A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles

Journal article

A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles

Smith, C. J.; Nikbin, N.; Ley, S. V.; Lange H.; Baxendale, I. R.

Org. Biomol. Chem. · 2011 · 9 · 1938–1947

Synthetic and heterocyclic chemistryAutomation and analyticsHazardous and reactive intermediates

Having demonstrated in the preceding publication the flow synthesis of aryl azides, we describe here a general protocol for the in-line purification of these versatile intermediates. As part of this investigation, we evaluated the use of ReactIR 45m as a tool…

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