Pauson–Khand Reactions in a Photochemical Flow Microreactor

Asano, Keisuke; Uesugi, Yuki; Yoshida, Junichi

doi:10.1021/ol4008519

Cited by 61 publications

(13 citation statements)

References 89 publications

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“…Yoshida et al have developed a continuous-flow protocol to make the methodology scalable. [75] A microreactor covered with a quartz glass was irradiated with a 80 W medium pressure Hg lamp. The majority of the reactions could be completed within 55 seconds.…”

Section: Direct Photochemical Activationmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

448

271

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Continuous-flow photochemistry is used increasingly by researchers in academia and industry to facilitate photochemical processes and their subsequent scale-up. However, without detailed knowledge concerning the engineering aspects of photochemistry, it can be quite challenging to develop a suitable photochemical microreactor for a given reaction. In this review, we provide an up-to-date overview of both technological and chemical aspects associated with photochemical processes in microreactors. Important design considerations, such as light sources, material selection, and solvent constraints are discussed. In addition, a detailed description of photon and mass-transfer phenomena in microreactors is made and fundamental principles are deduced for making a judicious choice for a suitable photomicroreactor. The advantages of microreactor technology for photochemistry are described for UV and visible-light driven photochemical processes and are compared with their batch counterparts. In addition, different scale-up strategies and limitations of continuous-flow microreactors are discussed.

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Section: Direct Photochemical Activationmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

448

271

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“…Another organometallic-mediated photochemical process using a flow microreactor system has been developed by Yoshida and coworkers for Pauson-Khand reactions [85].…”

Section: Miscellaneous Casesmentioning

confidence: 99%

Flow Technology for Organometallic-Mediated Synthesis

Degennaro¹,

Carlucci²,

Angelis³

et al. 2016

J Flow Chem

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“…In flash chemistry , using flow microreactors , extremely fast reactions can be conducted in a highly controlled manner. Extremely fast micromixing by virtue of short diffusion paths in a microspace is quite effective for conducting extremely fast reactions .…”

Section: Introductionmentioning

confidence: 99%

Monolithiation of 5,5′‐Dibromo‐2,2′‐bithiophene Using Flow Microreactors: Mechanistic Implications and Synthetic Applications

et al. 2019

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The lithiation of 5,5′‐dibromo‐2,2′‐bithiophene with one equivalent of an alkyllithium such as n‐BuLi or s‐BuLi was studied by varying the residence time in flow microreactors. With a short residence time, the product 2,2′‐bithiophene (3) derived from dilithiation was obtained preferentially and a significant amount of the starting material 5,5′‐dibromo‐2,2′‐bithiophene remained unchanged. An increase in the residence time caused a higher yield of the product 5‐bromo‐2,2′‐bithiophene derived from monolithiation with expense in the yields of 2,2′‐bithiophene and 5,5′‐dibromo‐2,2′‐bithiophene. The lithiation using MeLi gave the product 5‐bromo‐2,2′‐bithiophene preferentially even with a very short residence time.

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Pauson–Khand Reactions in a Photochemical Flow Microreactor

Abstract: Pauson-Khand reactions were achieved at ambient temperature without any additive using a photochemical flow microreactor. The efficiency of the reaction was better than that in a conventional batch reactor, and the reaction could be operated continuously for 1 h.

Cited by 61 publications

References 89 publications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Flow Technology for Organometallic-Mediated Synthesis

Monolithiation of 5,5′‐Dibromo‐2,2′‐bithiophene Using Flow Microreactors: Mechanistic Implications and Synthetic Applications

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