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5 article(s) from Watts, Paul

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

Cloudius R. Sagandira and
Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

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Scheme 1: Handling of azide chemistry in Tamiflu synthesis by Hayashi and co-workers [14].

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Figure 1: Synthesis of compound 2 from acyl chloride 1 via Curtius rearrangement using a continuous-flow syst...

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Scheme 2: Azide chemistry in the synthesis of Tamiflu.

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Scheme 3: Azidation of mesyl shikimate 5.

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Figure 2: Continuous-flow system for C-3 azidation of mesyl shikimate using aqueous sodium azide.

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Figure 3: Mesyl shikimate azidation conversion in a continuous-flow system using NaN₃.

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Figure 4: Desired azide 5 selectivity in a continuous-flow system using NaN₃.

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Figure 5: Effect of NaN₃ concentration on mesyl shikimate 4 conversion and azide 5 selectivity.

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Figure 6: Regio- and stereospecific nucleophilic -N₃ group attack.

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Figure 7: Continuous-flow system for C-3 azidation of mesyl shikimate using DPPA or TMSA.

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Figure 8: Mesyl shikimate azidation conversion in a continuous-flow system using DPPA.

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Figure 9: Desired azide 5 selectivity in a continuous-flow system using DPPA.

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Scheme 4: DPPA azidating mechanism in the presence of a base.

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Figure 10: Effect of TEA concentration on the reaction selectivity.

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Figure 11: Mesyl shikimate azidation conversion in a continuous-flow system using TMSA.

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Figure 12: Desired azide 5 selectivity in a continuous-flow system using TMSA.

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Figure 13: Continuous-flow system for C-3 azidation of mesyl shikimate using TBAA.

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Figure 14: Continuous-flow system for C-3 azidation of mesyl shikimate using TBAA.

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Scheme 5: C-5 azidation of acetamide 6 in our proposed route.

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Figure 15: Continuous flow system for C-5 azidation of acetamide 6 using NaN₃.

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Figure 16: Continuous-flow C-5 azidation of acetamide 6 using NaN₃.

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Figure 17: Continuous flow C-5 azidation of acetamide 6 using various azidating agents.

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Figure 18: Continuous flow synthesis of azide 7 from acetamide 6 using various azidating agents.

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Published 30 Oct 2019

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Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

Lubabalo Mafu,
Ben Zeelie and
Paul Watts

Beilstein J. Org. Chem. 2016, 12, 2046–2054, doi:10.3762/bjoc.12.193

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Scheme 1: Synthesis of menthol.

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Scheme 2: Synthesis of para-menthane-3,8-diol.

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Scheme 3: Synthesis of para-menthane diester derivatives.

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Figure 1: PMD conversion using stoichiometric quantities of acetic anhydride.

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Figure 2: Product distribution as a function of time.

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Figure 3: Product distribution as a function of time.

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Figure 4: Effect of molar ratio in product distribution.

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Scheme 4: Synthesis of para-menthane mono-ester derivatives.

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Published 19 Sep 2016

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The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

Faith M. Akwi and
Paul Watts

Beilstein J. Org. Chem. 2016, 12, 1987–2004, doi:10.3762/bjoc.12.186

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Scheme 1: PTSA-catalyzed diazotization and azo coupling reaction.

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Scheme 2: Ferric hydrogen sulfate (FHS) catalyzed azo compound synthesis.

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Scheme 3: Synthesis of azo compounds in the presence of silica supported boron trifluoride.

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Scheme 4: Phase transfer catalyzed azo coupling of 5-methylresorcinol in microreactors.

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Scheme 5: Synthesis of yellow pigment 12 in a micro-mixer apparatus.

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Scheme 6: Continuous flow synthesis of Sudan II azo dye in LTF-MS microreactors.

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Figure 1: pH profile plot at constant flow rate of 0.03 mL/min.

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Figure 2: pH profile plot at a constant flow rate of 0.7 mL/min.

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Scheme 7: Azo coupling reaction under acidic conditions.

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Figure 3: pH profile plot at a constant flow rate of 0.03 mL/min.

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Figure 4: pH profile plot at constant flow rate of 0.7 mL/min.

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Figure 5: Temperature profile plot at constant pH 5.66.

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Figure 6: Schematic representation of the microreactor set up.

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Figure 7: Schematic representation of the microreactor set up.

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Figure 8: Scaled up microreactor set up: PTFE tubing i.d. 1.5 mm a) Chemyx Fusion 100 classic syringe pump, b...

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Published 06 Sep 2016

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Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S_NAr reaction

Charlotte Wiles and
Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

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Figure 1: Illustration of synthetically interesting diaryl ethers.

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Scheme 1: Illustration of the model reaction used to compare the enabling technologies of microwave and micro...

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Scheme 2: Illustration of the model reaction used to benchmark Labtrix S1 against batch and stopped-flow micr...

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Figure 2: Photograph illustrating Labtrix^® S1, the automated microreactor development apparatus from Chemtrix...

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Figure 3: Schematic illustrating the 10 µL reactor manifold used for the S_NAr reactions described herein (322...

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Figure 4: Schematic illustration of the reactor manifold used to evaluate the continuous-flow synthesis of 2-...

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Figure 5: Comparison of the results obtained in Labtrix^® S1 with reported data generated in a microwave synth...

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Figure 6: Screen shot from the Labtrix^® S1 control software illustrating the system file that enables the use...

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Figure 7: Summary of the results obtained for the organic base screen towards the S_NAr reaction between DCNB (...

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Figure 8: Illustration of the substituent effect on the synthesis of diaryl ethers under continuous flow (res...

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Figure 9: Schematic illustrating the mixing of immiscible reagent streams in a microfluidic channel, whereby ...

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Figure 10: Comparison of base effect on the synthesis of 2-chloro-1-(4-methoxyphenoxy)-4-nitrobenzene (7) (res...

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Figure 11: Graphical representation of an automated flow reaction for equilibration and screening of reactor t...

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Published 04 Oct 2011

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The development and evaluation of a continuous flow process for the lipase- mediated oxidation of alkenes

Charlotte Wiles,
Marcus J. Hammond and
Paul Watts

Beilstein J. Org. Chem. 2009, 5, No. 27, doi:10.3762/bjoc.5.27

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Scheme 1: Illustration of the chemo-enzymatic epoxidation of an alkene; involving the biocatalytic perhydroly...

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Scheme 2: Illustration of the chemo-enzymatic epoxidation of 1-methylcyclohexene (6) to 1-methylcyclohexene o...

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Scheme 3: Model reaction used to compare the continuous flow epoxidation strategy with the conventional batch...

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Figure 1: Schematic of the reaction set-up used to evaluate the continuous flow chemo-enzymatic epoxidation o...

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Figure 2: Graph illustrating the effect of flow rate (hence residence time) on the conversion of 1-methylcycl...

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Figure 3: Graph illustrating the effect of (a) flow rate and (b) residence time on the conversion of 1-methyl...

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Figure 4: Graph illustrating the effect of oxidant stoichiometry on the conversion of 1-methylcyclohexene (6)...

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Figure 5: Illustration of the enzyme 4 stability to H₂O₂ (2) for the conversion of 1-methylcyclohexene (6) to...

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Scheme 4: Illustration of the reaction products obtained when conducting the continuous flow epoxidation of c...

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Published 02 Jun 2009

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Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated SNAr reaction

The development and evaluation of a continuous flow process for the lipase- mediated oxidation of alkenes

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S_NAr reaction