Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN
Flow chemistry has shown significant versatility over the last two decades, offering advantages in efficiency, scalability, and sustainability. In this study, the continuous stirred tank reactor (CSTR) was used to optimise the synthesis of α-hydroxyphosphonates via the Pudovik reaction and their sub...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-11-01
|
| Series: | Reactions |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2624-781X/5/4/42 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1846102963642171392 |
|---|---|
| author | Joseph Dean Natalia Buckler Reinoso Francesco Spiedo Carola Romero Fernández Bhaven Patel |
| author_facet | Joseph Dean Natalia Buckler Reinoso Francesco Spiedo Carola Romero Fernández Bhaven Patel |
| author_sort | Joseph Dean |
| collection | DOAJ |
| description | Flow chemistry has shown significant versatility over the last two decades, offering advantages in efficiency, scalability, and sustainability. In this study, the continuous stirred tank reactor (CSTR) was used to optimise the synthesis of α-hydroxyphosphonates via the Pudovik reaction and their subsequent conversion to phosphates through the phospha-Brook rearrangement. The study highlights that using CSTRs allows for better control over reaction parameters, leading to reduced reaction times and improved yields compared to traditional batch methods. The optimised conditions successfully facilitated a range of organophosphates, including electron-rich and electron-poor derivatives, with high efficiency. Additionally, a one-pot tandem process combining the Pudovik reaction and the phospha-Brook rearrangement was developed, reducing reaction times to two hours while maintaining comparable yields. This work demonstrates the potential of CSTRs in flow chemistry for synthesising complex organophosphorus compounds, achieving higher reaction yields and shorter reaction times, highlighting the effectiveness of continuous flow methodologies. |
| format | Article |
| id | doaj-art-dd23e53ca76247468d0564d891ee28d7 |
| institution | Kabale University |
| issn | 2624-781X |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Reactions |
| spelling | doaj-art-dd23e53ca76247468d0564d891ee28d72024-12-27T14:49:59ZengMDPI AGReactions2624-781X2024-11-015481282210.3390/reactions5040042Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBNJoseph Dean0Natalia Buckler Reinoso1Francesco Spiedo2Carola Romero Fernández3Bhaven Patel4Applied Chemistry & Pharmaceutical Technology (ADAPT), School of Human Sciences, London Metropolitan University, London N7 8DB, UKApplied Chemistry & Pharmaceutical Technology (ADAPT), School of Human Sciences, London Metropolitan University, London N7 8DB, UKApplied Chemistry & Pharmaceutical Technology (ADAPT), School of Human Sciences, London Metropolitan University, London N7 8DB, UKApplied Chemistry & Pharmaceutical Technology (ADAPT), School of Human Sciences, London Metropolitan University, London N7 8DB, UKApplied Chemistry & Pharmaceutical Technology (ADAPT), School of Human Sciences, London Metropolitan University, London N7 8DB, UKFlow chemistry has shown significant versatility over the last two decades, offering advantages in efficiency, scalability, and sustainability. In this study, the continuous stirred tank reactor (CSTR) was used to optimise the synthesis of α-hydroxyphosphonates via the Pudovik reaction and their subsequent conversion to phosphates through the phospha-Brook rearrangement. The study highlights that using CSTRs allows for better control over reaction parameters, leading to reduced reaction times and improved yields compared to traditional batch methods. The optimised conditions successfully facilitated a range of organophosphates, including electron-rich and electron-poor derivatives, with high efficiency. Additionally, a one-pot tandem process combining the Pudovik reaction and the phospha-Brook rearrangement was developed, reducing reaction times to two hours while maintaining comparable yields. This work demonstrates the potential of CSTRs in flow chemistry for synthesising complex organophosphorus compounds, achieving higher reaction yields and shorter reaction times, highlighting the effectiveness of continuous flow methodologies.https://www.mdpi.com/2624-781X/5/4/42continuous flowPudovik reactionphospha-Brook rearrangementα-hydroxyphosphonatesphosphates1,5-diazabicyclo(4.3.0)non-5-ene |
| spellingShingle | Joseph Dean Natalia Buckler Reinoso Francesco Spiedo Carola Romero Fernández Bhaven Patel Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN Reactions continuous flow Pudovik reaction phospha-Brook rearrangement α-hydroxyphosphonates phosphates 1,5-diazabicyclo(4.3.0)non-5-ene |
| title | Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN |
| title_full | Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN |
| title_fullStr | Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN |
| title_full_unstemmed | Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN |
| title_short | Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN |
| title_sort | continuous flow optimisation of the pudovik reaction and phospha brook rearrangement using dbn |
| topic | continuous flow Pudovik reaction phospha-Brook rearrangement α-hydroxyphosphonates phosphates 1,5-diazabicyclo(4.3.0)non-5-ene |
| url | https://www.mdpi.com/2624-781X/5/4/42 |
| work_keys_str_mv | AT josephdean continuousflowoptimisationofthepudovikreactionandphosphabrookrearrangementusingdbn AT nataliabucklerreinoso continuousflowoptimisationofthepudovikreactionandphosphabrookrearrangementusingdbn AT francescospiedo continuousflowoptimisationofthepudovikreactionandphosphabrookrearrangementusingdbn AT carolaromerofernandez continuousflowoptimisationofthepudovikreactionandphosphabrookrearrangementusingdbn AT bhavenpatel continuousflowoptimisationofthepudovikreactionandphosphabrookrearrangementusingdbn |