Basic Concepts of “Cation Pool” and “Cation Flow” Methods and Their Applications in Conventional and Combinatorial Organic Synthesis

Yoshida, Jun; Suga, Seiji

doi:10.1002/1521-3765(20020617)8:12<2650::aid-chem2650>3.0.co;2-s

Cited by 213 publications

(93 citation statements)

References 7 publications

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“…Yoshida et al [52,53] developed a unique ''cation-flow'' method and applied it to combinatorial organic syntheses. Carbocations play an important role in organic synthesis.…”

Section: Sequential Micro Reaction Systemsmentioning

confidence: 99%

“…Schematic diagram of the ''cation-flow'' system. [52] Figure 14. An electrochemical micro-flow reactor for the ''cation-flow'' method.…”

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

“…An electrochemical micro-flow reactor for the ''cation-flow'' method. [52] conventional pumps, injection valves, or an autosampling machine are required for introducing reagent segments to the microchips. Consequently, the advantages of micro reaction systems over already existing automated reaction systems are not so clear.…”

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

“…Experiments in combinatorial synthesis using a micro chemical system, in which reactions that cannot be realized in conventional reactors are carried out, are also desirable, because they may propel research on miniaturized device development. The unique ''cationflow'' micro electrochemical synthesis done by Yoshida et al [52,53] is of great value from this viewpoint.…”

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

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Micro‐Flow Reaction Systems for Combinatorial Syntheses

Kitamori

2003

Macromol. Rapid Commun.

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Summary: Micro‐flow chemical processes, which are attracting great attention lately, offer more than the advantage of size. In microspaces, mass and heat transfer lengths are short, the specific interfacial area is large, and heat capacity is remarkably small compared with the situation in conventional scale reaction vessels. These characteristics make precise control of reaction conditions possible, and higher selectivity and conversion can be obtained. In some cases, reactions that are too dangerous to be carried out on a conventional scale can be safely done using micro‐flow reaction systems. Recently, some researchers have developed basic model systems for solution‐phase combinatorial synthesis by utilizing micro‐flow chemical processes. There are two types of combinatorial synthesis systems using micro‐flow chemical processes: parallel reaction systems and sequential reaction systems. In parallel reaction systems, components in starting libraries are simultaneously mixed in all possible combinations by using many micro reaction channels. In addition to needing as many pumps as the starting materials and as many reaction channels as members of the product library, complicated three‐dimensional piping is necessary to connect the pumps and the micro reaction channels. In sequential reaction systems, segments of starting materials are sequentially injected and reacted in a single micro reaction channel in all possible combinations. The latter systems are usually smaller than the former, however, relatively large fluid control devices are necessary in both of them, and improvement of micro‐fluid‐control devices is a critical issue for putting micro‐combinatorial‐synthesis systems to practical use.Parallel micro‐flow reaction system made up of multiple micro chemical chips for combinatorial 2 × 2 synthesis.magnified imageParallel micro‐flow reaction system made up of multiple micro chemical chips for combinatorial 2 × 2 synthesis.

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“…Yoshida et al [52,53] developed a unique ''cation-flow'' method and applied it to combinatorial organic syntheses. Carbocations play an important role in organic synthesis.…”

Section: Sequential Micro Reaction Systemsmentioning

confidence: 99%

“…Schematic diagram of the ''cation-flow'' system. [52] Figure 14. An electrochemical micro-flow reactor for the ''cation-flow'' method.…”

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

Section: Concluding Remarks and Perspectivesmentioning

confidence: 99%

See 2 more Smart Citations

Micro‐Flow Reaction Systems for Combinatorial Syntheses

Kitamori

2003

Macromol. Rapid Commun.

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“…(For recent papers on organic electrosynthesis, see for example, refs [16][17][18] Electrochemical oxidation in solvents normally used in organic syntheses can be carried out by the cation pool method. [19][20][21] We have reported that the electrochemical oxidation of diaryl disulfides (ArSSAr) leads to the formation of ArS(ArSSAr) + , which can be accumulated in solution at low temperatures ( Figure 1). [22][23][24][25][26] This reaction presumably proceeds by generation of "ArS + " followed by its reaction with ArSSAr.…”

Section: Introductionmentioning

confidence: 99%

Generation and reactions of thiirenium ions by the Cation Pool method

Shimizu¹,

Horiuchi²,

Hayashi³

et al. 2017

Arkivoc

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Thiirenium ions generated and accumulated by low-temperature electrochemical oxidation of disulfides in the presence of alkynes were successfully observed by low-temperature NMR, Raman, and mass spectroscopies and were found to be stable at temperatures below −40 °C. The thiirenium ions showed ambident reactivity toward subsequently added nucleophiles to give either disubstituted alkenes or alkynes depending on the nature of the nucleophiles.

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Radical Cation Fragmentation Reactions in Organic Synthesis

Poniatowski

Floreancig

2009

Carbon‐Centered Free Radicals and Radical Cations

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Basic Concepts of “Cation Pool” and “Cation Flow” Methods and Their Applications in Conventional and Combinatorial Organic Synthesis

Cited by 213 publications

References 7 publications

Micro‐Flow Reaction Systems for Combinatorial Syntheses

Micro‐Flow Reaction Systems for Combinatorial Syntheses

Generation and reactions of thiirenium ions by the Cation Pool method

Radical Cation Fragmentation Reactions in Organic Synthesis

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