Microwave Heated Continuous Flow Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones

Skillinghaug, Bobo; Rydfjord, Jonas; Sävmarker, Jonas; Larhed, Mats

doi:10.1021/acs.oprd.6b00306

Cited by 24 publications

(10 citation statements)

References 59 publications

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“…Such systems were expected to become powerful tools in organic synthesis [18]. Indeed, there have been several reports on organic synthesis in this context such as Pd-catalyzed C-C bond formations [20][21][22][23][24], biodiesel synthesis [25][26][27][28][29] and others [30][31][32][33], using a flow-type MW device. Flow-type MW heating in a microcapillary reactor has also been utilized in various reactions [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

A continuous-flow resonator-type microwave reactor for high-efficiency organic synthesis and Claisen rearrangement as a model reaction

et al. 2018

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We have developed a single-mode microwave reactor for continuous-flow synthesis with various methods of operation. This device measures the resonant frequency and modulates the oscillation frequency accordingly to maintain the maximum electric field intensity in the cavity. It can be operated either using constant applied irradiation power or using new programs which change the electric power (E-GRA) and change the flow rate (Fl-GRA), in order to rapidly screen various reaction conditions. As a model reaction, the Claisen rearrangement reaction of allyl 1-naphthyl ether 1 was rapidly optimized in this device, affording the desired product 2-allylnapthalen-1-ol 2 in high (91%) yield and up to 20 g/h productivity.

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Section: Introductionmentioning

confidence: 99%

A continuous-flow resonator-type microwave reactor for high-efficiency organic synthesis and Claisen rearrangement as a model reaction

et al. 2018

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“…In 2016, Larhead and co-workers utilised a transparent aluminium oxide microwave reactor for the Pd(II)-catalysed desulfitative synthesis of aryl ketones in continuous flow (Scheme 35). 53…”

Section: Review Syn Thesismentioning

confidence: 99%

Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis

Markovič¹,

Lopatka²,

Gracza³

et al. 2020

Synthesis

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Considerable advances have been made using continuous flow chemistry as an enabling tool in organic synthesis. Consequently, the number of articles reporting continuous flow methods has increased significantly in recent years. This review covers the progress achieved in homogeneous palladium catalysis using continuous flow conditions over the last five years, including C–C/C–N cross-coupling reactions, carbonylations and reductive/oxidative transformations.1 Introduction2 C–C Cross-Coupling Reactions3 C–N Coupling Reactions4 Carbonylation Reactions5 Miscellaneous Reactions6 Key to Schematic Symbols7 Conclusion

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“…Various reactions were reported such as Pd catalyzed couplings (oxidative Heck reaction, Suzuki reaction), heterocyclic compound syntheses and Fischer indole syntheses. Using this reactor, the Claisen rearrangement of 10 gave 11 in 99 % yield, 2.2 g/h and the Diels‐Alder cycloaddition of 12 and 13 gave 14 in 52 % yield, 1.1 g/h (Figure ) –…”

Section: Reactor and Reaction Examples For Different Modes Of Mw Heatmentioning

confidence: 99%

Microwave Flow: A Perspective on Reactor and Microwave Configurations and the Emergence of Tunable Single‐Mode Heating Toward Large‐Scale Applications

Barham

Koyama

Norikane

et al. 2018

The Chemical Record

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Microwave heating in chemical reactions was first reported in 1986. There have since been many reports employing microwave heating in organic chemistry, where microwave heating has afforded higher yields of products in shorter time periods. However, such reactions are challenging to scale in batch due to the limited penetration depth of microwaves as well as the wave propagation dependence on cavity size. Continuous flow has addressed both these issues, enabling scalability of microwave processes. As such, a host of reports employing microwave flow chemistry have emerged, employing various microwave heating and reactor configurations in the context of either custom-built or commercial apparatus. The focus of this review is to present the benefits of microwave heating in the context of continuous flow and to characterize the different types of microwave flow apparatus by their design (oscillator, cavity type and reactor vessel). We advocate the adoption of tunable, solid-state oscillator single-mode microwave flow reactors which are more versatile heaters, impart better process control and energy efficiency toward laboratory and larger-scale synthetic chemistry applications.

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Microwave Heated Continuous Flow Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones

Cited by 24 publications

References 59 publications

A continuous-flow resonator-type microwave reactor for high-efficiency organic synthesis and Claisen rearrangement as a model reaction

A continuous-flow resonator-type microwave reactor for high-efficiency organic synthesis and Claisen rearrangement as a model reaction

Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis

Microwave Flow: A Perspective on Reactor and Microwave Configurations and the Emergence of Tunable Single‐Mode Heating Toward Large‐Scale Applications

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