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Peer-Review Record

Suzuki–Miyaura Coupling Using Monolithic Pd Reactors and Scaling-Up by Series Connection of the Reactors

Reviewer 1: Anonymous
Reviewer 2: Anonymous
Reviewer 3: Anonymous
Reviewer 4: Anonymous
Catalysts 2019, 9(3), 300; https://doi.org/10.3390/catal9030300
Received: 2 March 2019 / Revised: 14 March 2019 / Accepted: 19 March 2019 / Published: 25 March 2019
(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

Round 1

Reviewer 1 Report

Suggestions to the authors:

1.-In this work, the authors studied the best reactor structuration to carried out the Suzuki-Miyaura reaction. Nevertheless, they didn´t explain what does this reaction consist of. A scheme about this process must be included to better understand the purpose of this work.

2.- When supported palladium catalysts are used the Suzuki–Miyaura cross-coupling reaction is a heterogeneous  catalysis. In this scenario and during the reaction, palladium could be released from the surface of the solid support and this palladium could be responsible of the like quasi-homogeneous catalysis. How the authors avoided this undesirable situation ?


Author Response

I attached a file on our reply.

Author Response File: Author Response.pdf

Reviewer 2 Report

This article represents an extension of reference 19, in which Palladium-catalyzed cross coupling reactors have been developed at high flow rates. The research area is worthy of research and the article has been carefully written, providing a smart and efficient approach for the synthesis of biaryl products in sustainable conditions. Minor comments:

1) Results ad discussion and experimental part

- Explanation of Table 1 must be improve:

                - explain differences between a and b conditions (monolith A and B?)

                - explain why in some cases conversion are not given (entry 15) and just isolated yields, maybe attribute to the high boiling point of products

                - the authors should explain the trends observed with pattern substitutions in the aromatic ring heteroaromatic substitutions…

                - retentions times for reactants are missing in the experimental section or supporting information, just the ones for final products are given in the experimental section

- Define yields in Tables 2-6 and how they were measured (GC analyses)

2) Reference section:

- reference 1b: Wiley instead of Wiely

- reference 6a: delete 10 as this is the issue not the volume number

- reference 11c: Molecules instead of molecules

- reference 23a: Angew. Chem. Int. Ed. instead of AICHE

- delete reference 25

- reference 31: delete 4 as this is the issue not the volume number

- reference 36: delete 4 as this is the issue not the volume number

3) Supporting information: A table with the retention times and chromatograms should be given to complement the NMR spectra.


Author Response

I attached a file on our reply.

Author Response File: Author Response.pdf

Reviewer 3 Report

In the interesting manuscript, the authors describe an efficient method of unsymmetrical biaryls synthesis by integrating lithiation, borylation, and Suzuki–Miyaura coupling using a flow reactor packed a Pd catalyst supported by the polymer monolith. It was also found that the series connection of flow reactors was proved to be a method for numbering-up of flow reactors for scale-up. The method has been successfully used in various cross-coupling reactions, mainly in coupling of functional aryl and heteroaryl iodides as well as to a gram-scale synthesis of adapalene.

In my opinion, the presented manuscript is well written; the study was properly planned and carried out. The authors conducted an exhaustive discussion of the results and carried out the correct characterization of the obtained compounds. With the above in mind, I recommend this manuscript for publication in Catalysts in its current form.


Author Response

I attached a file on our reply.

Author Response File: Author Response.pdf

Reviewer 4 Report

The paper “Suzuki–Miyaura Coupling Using Monolithic Pd Reactors and Scaling-up by Series Connection of the Reactors” deals with an important subject aimed at the space integration of several steps (lithiation of aryl halides, borylation of aryllithiums) with Suzuki–Miyaura reaction using Pd catalyst supported by a polymer monolith flow reactor. As the authors point out by themselves, they report the full details of the work completed and published three years ago (Nagaki, A.; Hirose, K.; Moriwaki, Y.; Mitamura, K.; Matsukawa, K.; Ishizuka, N.; Yoshida, J., Integration of borylation of aryllithiums and Suzuki-Miyaura coupling using monolithic Pd catalyst. Catalysis Science & Technology 2016, 6, (13), 4690-4694.). Indeed, the reviewed paper is mainly a compilation of the main text of the article published in Catalysis Science & Technology and the text from the Electronic Supplementary Material to the same article, including figures, tables, experimental details, etc.

 

In fact, in a reviewed article for Catalysts, only data for an additional type of polymer monolith B (different from polymer monolith A only by annealing temperature) are new. I do not doubt about high quality of the material reviewed by the experts of Catalysis Science & Technology, and I see no points in reviewing this work for the second time. The paper can be recommended for publication in Catalysts, if the publication policy of the Catalysts journal allows publishing this kind of works. But the data presented with such level of similarity (self-plagiarism) cannot be considered as completely new.


Author Response

I attached a file on our reply.

Author Response File: Author Response.pdf

Round 2

Reviewer 1 Report

Reviewer considers acceptable the authors comments regarding the questions proposed in the previous version of this manuscript.


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