Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis

2018 ◽  
Vol 22 (6) ◽  
pp. 741-746 ◽  
Author(s):  
Hirotsugu Usutani ◽  
David G. Cork
Keyword(s):  
Boronic Acid ◽  
Scale Up ◽  
Flow Chemistry ◽  
Acid Synthesis ◽  
Side Reactions ◽  
Effective Utilization

Development and Scale-up of a Flow Chemistry Lithiation–Borylation Route to a Key Boronic Acid Starting Material

2017 ◽  
Vol 21 (4) ◽  
pp. 669-673 ◽  
Author(s):  
Hirotsugu Usutani ◽  
Takashi Nihei ◽  
Charles D. Papageorgiou ◽  
David G. Cork
Keyword(s):  
Boronic Acid ◽  
Scale Up ◽  
Flow Chemistry ◽  
Starting Material

8 Scale-up of flow chemistry system

2021 ◽  
pp. 229-258
Author(s):  
Kai Wang ◽  
Jian Deng ◽  
Chencan Du ◽  
Guangsheng Luo
Keyword(s):  
Scale Up ◽  
Flow Chemistry

scholarly journals Rapid approach to complex boronic acids

2019 ◽  
Vol 5 (7) ◽  
pp. eaaw4607 ◽  
Author(s):  
Constantinos G. Neochoritis ◽  
Shabnam Shaabani ◽  
Maryam Ahmadianmoghaddam ◽  
Tryfon Zarganes-Tzitzikas ◽  
Li Gao ◽  
...  
Keyword(s):  
Small Molecules ◽  
Boronic Acid ◽  
Multicomponent Reactions ◽  
Chemical Space ◽  
Building Blocks ◽  
Acid Synthesis ◽  
Success Rates ◽  
Boronic Acid Derivatives ◽  
Low Coverage ◽  
Target Synthesis

The compatibility of free boronic acid building blocks in multicomponent reactions to readily create large libraries of diverse and complex small molecules was investigated. Traditionally, boronic acid synthesis is sequential, synthetically demanding, and time-consuming, which leads to high target synthesis times and low coverage of the boronic acid chemical space. We have performed the synthesis of large libraries of boronic acid derivatives based on multiple chemistries and building blocks using acoustic dispensing technology. The synthesis was performed on a nanomole scale with high synthesis success rates. The discovery of a protease inhibitor underscores the usefulness of the approach. Our acoustic dispensing–enabled chemistry paves the way to highly accelerated synthesis and miniaturized reaction scouting, allowing access to unprecedented boronic acid libraries.

scholarly journals Continuous-Flow Catalysis

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1066
Author(s):  
Sándor B. Ötvös
Keyword(s):  
Chemical Reactions ◽  
Continuous Flow ◽  
Scale Up ◽  
Flow Chemistry ◽  
The Past

During the past twenty years, flow chemistry has emerged as an enabling tool to simplify, accelerate, integrate, scale-up and automatize chemical reactions [...]

scholarly journals Scale-Up of Polymerization Process of Biodegradable Polymer Poly(lactic acid) Synthesis Using Direct Polycondensation Method

2015 ◽  
Vol 3 (2) ◽  
pp. 100-109
Author(s):  
Sommai Pivsa-Art ◽  
Sumonman Niamlang ◽  
Weraporn Pivsa-Art ◽  
Nutchapon Santipatee ◽  
Tossamon Wongborh ◽  
...  
Keyword(s):  
Lactic Acid ◽  
Biodegradable Polymer ◽  
Scale Up ◽  
Acid Synthesis ◽  
Polymerization Process ◽  
Poly Lactic Acid ◽  
Direct Polycondensation

scholarly journals Electrosynthesis of 3,3′,5,5’-Tetramethyl-2,2′-biphenol in Flow

2020 ◽  
Author(s):  
Maximilian Selt ◽  
Barbara Gleede ◽  
Robert Franke ◽  
Andreas Stenglein ◽  
Siegfried R. Waldvogel
Keyword(s):  
Scale Up ◽  
Transition Metal Catalysis ◽  
Side Reactions ◽  
Narrow Gap ◽  
Metal Catalysis ◽  
Gap Flow ◽  
Electrolysis Cells ◽  
Efficient Alternative ◽  
Synthetic Approaches ◽  
Work Up

Abstract3,3′,5,5’-Tetramethyl-2,2′-biphenol is well known as an outstanding building block for ligands in transition-metal catalysis and is therefore of particular industrial interest. The electro-organic method is a powerful, sustainable, and efficient alternative to conventional synthetic approaches to obtain symmetric and non-symmetric biphenols. Here, we report the successive scale-up of the dehydrogenative anodic homocoupling of 2,4-dimethylphenol (4) from laboratory scale to the technically relevant scale in highly modular narrow gap flow electrolysis cells. The electrosynthesis was optimized in a manner that allows it to be easily adopted to different scales such as laboratory, semitechnical and technical scale. This includes not only the synthesis itself and its optimization but also a work-up strategy of the desired biphenols for larger scale. Furthermore, the challenges such as side reactions, heat development and gas evolution that arose during optimization are also discussed in detail. We have succeeded in obtaining yields of up to 62% of the desired biphenol.

scholarly journals Combining Radial and Continuous Flow Synthesis to Optimize and Scale-up the Production of Medicines

2021 ◽  
Author(s):  
Mara Guidi ◽  
Soo-Yeon Moon ◽  
Lucia Anghileri ◽  
Dario Cambié ◽  
Peter Seeberger ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Scale Up ◽  
Flow Chemistry ◽  
Essential Medicines ◽  
Flow Synthesis ◽  
Drug Production ◽  
On Demand ◽  
Current Drug

Current drug production in batch cannot adapt rapidly to market demands, evidenced by recent shortages in many markets globally of essential medicines. Flow chemistry is a valuable tool for on-demand...

Cyclosiloxane polymer bearing dynamic boronic acid: synthesis and bottom-up nanocoating

2019 ◽  
Vol 10 (38) ◽  
pp. 5228-5235 ◽  
Author(s):  
Soyeon Kim ◽  
Huie Zhu ◽  
Ali Demirci ◽  
Shunsuke Yamamoto ◽  
Tokuji Miyashita ◽  
...  
Keyword(s):  
Film Thickness ◽  
Self Assembly ◽  
Boronic Acid ◽  
Metal Ion ◽  
Acid Synthesis ◽  
Covalent Bonding ◽  
Bottom Up ◽  
Ion Sensor ◽  
Polymer Bearing

Boronic acid-containing polycyclosiloxane showed unique self-assembly nanofilm formation (6 nm film thickness) on various substrates and provided film-based metal ion sensor capability through dynamic covalent bonding.

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