Talk:Suzuki reaction

Mechanism

The drawn mechanism is a misreading of [1] In that paper's abstract, it is made clear that the action of RO(-) is to *inhibit* the transmetallation, not facilitate it. I will create a new drawing for this. Hansonrstolaf (talk) 10:20, 15 April 2021 (UTC)

I don't think that the transmetalation should be shown to proceed from the boronate. There are several studies on the role of alkoxide bases, summarised in this review by Lloyd-Jones, which show that (apart from 9-BBN) "[...] there is scant evidence for significant catalytic turnover through the boronate pathway". More detailed information on possible Pd-O-B intermediates can be found in a 2016 study by Denmark, but that's maybe a bit too obscure to discuss in detail. Cato82 (talk) 15:36, 1 September 2023 (UTC)

Peer review and responses during the educational assignment in Fall 2013

These are my comments regarding your newly updated page on Suzuki Coupling:

• I would change “Pd(0)” to “L₂-Pd⁰”, since some (but not all) Suzuki Coupling reactions involve ligands on the palladium metal center (such as L = PPh₃)

• The last sentence of your “Reaction mechanism” section and the first sentence of your “Oxidative Addition” section do not jive with one another. Consider revising.

• I don’t think you need to sign your name next to every section you’ve revised. Not necessary.

• R2-Pdll-OtBu from R2-Pdll-X needs to be formatted correctly. There are subscript and superscript options in the editing tools. For example, should read R₂-Pd^II-Ot Bu.

• "Reductive Elimination" section needs more work (should be clearer). In particular, the ranking of various metal centers should be worded more clearly to better understand what you are comparing.

• First sentence of “applications” section should be re-worded (“moved into use” is awkward).

• What are “fine chemicals?” Describe this.

• What is a “CNS” agent? Describe this.

• Your mechanism directly above the “Variations” section should have the change in isomerization of the Pd-alkene intermediate (going from cis to trans) prior to the last step. It is slightly unclear how you end up with trans coupling given the structure prior to the product formation.

• The next to last sentence in the “Metal catalyst” subsection of “variations” section needs reworded (awkward wording).

• There’s a typo in the “Other Variations” subsection (in the middle of the section).

• In the “Other Variations” subsection, non-toxic should have a hyphen in between “non” and “toxic”

• In the last section, “Hence, this reaction is beneficial for having relatively cheap reagents, easy to prepare, and green” should be changed to “...and practicing “green chemistry." for the last part of the sentence.

AviMole602 (talk)

Peer Review

This Wikipedia page is loaded with useful information. It may be so loaded with information that it may be close to being considered overeloaded. The writers did an excellent job of including important topics that were not covered on the original page while integrating the previous material in a nice fashion. However, some things could be changed around a bit in order to make it more organized as well as more “wikipedia-ish.”

Introduction

The addition to the introduction provides good, relevant information, and I would only suggest some minor improvements. The first paragraph (“The Suzuki reaction is the organic reaction . .. ) and the third paragraph (“First published in 1979 . . . ) seem to be redundant in their definition of the reaction. Both mention how it employs a palladium catalyst, boronic acid, and halides or pseudo-halides. This just needs to be condensed. I think that you do not need to go into too much description about the metal catalyst (pre-catalyst, 4-coordinate, etc) in the introduction. It would fit better in an actual section. Lastly, I would recommend adding the one thing that defines the reaction – its base dependence. You mention this later under your “Kinetics” section, but it is a good general aspect of the reaction that would fit nicely in the introduction.

Reaction Mechanism

These sections provide good, concise, relevant information. Again, only a few minor suggestions. You mention in the reaction mechanism section that the rate determining step is either the oxidative addition or the transmetalation, but in your oxidative addition section you say that it’s the rate determining step but make no mention of it in the transmetalation section? In your reductive elimination section, metals are ordered in terms of their relative rates for reductive elimination, but it is unclear if that is for the Suzuki reaction or in general. This seems random and out of place unless you introduce the information and mention its relevance for the reaction. It’s good information, it just needs to be put in context. I would recommend that you consider renaming the kinetics section to something like “role of the base” because it is talking about kinetics, but it seems to primarily be concerned with the role of the base in the reaction mechanism and its effect on the kinetics. Lastly, I would move your mention of stereochemistry out of the applications section and into the reaction mechanism section as a new topic entitled “stereochemistry.” When I read the page initially, I was wondering why there was no mention of it here. When I continued reading, I found it in the applications section but felt like it was not only out of place but that it should have been mentioned earlier.

Applications

Consider breaking this section up into “Industrial Applications” and “Synthetic Applications.” There is a good general description and then your text can naturally be broken into these two sections because it is presented in that order. This is not at all necessary, but it may make the page more easy to navigate.

Variations

My comment about making this page more “Wikipedia-ish” was really in regards to this section. There is a lot of information here, but it may be too much for the Wikipedia audience. Your information is presented more like a review than a Wikipedia page. Since you already gave the link to the review, you may not need to include a case-by-case analysis of the development of nickel-catalyzed Suzuki reactions. Rather, you might consider using this section as a comparison of nickel versus palladium catalysts. I’m suggesting this because this section was the most difficult section to follow and understand what the current nickel catalyst is capable of. The information I got from it is that nickel is better than palladium because it is less expensive and has a greater substrate scope. However, more catalyst and ligand are required in the case of nickel, and it is air and moisture sensitive, but apparently these problems have been fixed?

Advantages

This is a great section but may be better placed after reaction mechanism and before application mainly because it is the advantages that lead to the industrial and synthetic applications.

Figures

Your figures are very nicely sketched and relevant. I have some minor recommendations that may make the message in your figures more clear. For your reaction mechanism, adding the words to the steps really helps! One suggestion is moving transmetalation because it looks like it is describing borane reduction. Labeling the molecules in your synthesis schemes in the applications section also be helpful (CI-1034 and CNS agent). Also consider not using the acronym for CNS or adding a link as well as including the actual name of the compound.

References

There were a significant amount of references added to the page. Although the majority come from journal sources this seems to be inevitable due to the nature of the topic.

ajc540 (talk)

Another Peer Review

Some suggestions from UMChemProfessor (talk) 19:44, 4 November 2013 (UTC)

Overall, the peer reviews are excellent and their advice should be used to improve the site.

In addition, I have a few suggestions:

1. The introductory paragraph has some details which are probably better placed later within the site. For example, the information on the leaving groups. Try to keep this section at the level of a high school student.
2. The section on "kinetics" can be merged with the appropriate mechanism sections.
3. The "advantages" could also be integrated into another section(s).
4. There is no consistency between the figures, some have bolder font/lines than others, and the molecule sizes are all different.

Suggestions from ChemLibrarian (talk) 15:56, 5 November 2013 (UTC)

1. I see your images have a mixed file types (.png and .jpeg). Actually, Wikipedia recommends "The basic choices are SVG for simple diagrams (especially those that need to be scaled), JPEG for photographic images, and PNG for everything else" as discussed on this page Wikipedia:Preparing images for upload. So, if you drew these diagrams in ChemDraw, it's better to save them as .png . If you are using other tools allowing saving as .svg, that would be the best.
2. Some of the images were not uploaded to Wikimedia Commons but uploaded to Wikipedia instead. Please consider move them to Wikimedia Commons.
3. Some of the references are not formatted right, like 5 and 6.
4. Please remember to delete your signatures at various places when you move the article to a formal Wikipedia page.

Responses to Peer Edit Reviews

AviMole602

Thanks for your review! Here is what we have edited and worked on: We have changed all of the palladium complexes to include the ligands in a general or specific way (L or PPh₃). We have changed the discrepancy in the talk of the rate limiting step in the two locations. The signatures have been removed. The formatting of the complexes and compounds should be corrected in the article. We worked on the reductive elimination section and also referenced to the wikipedia article that talks about the general reductive elimination step in a mechanism. The rankings of the metals has been removed as we agree that it did not fit in that section. We have reworded the first sentence and other parts of our industrial applications page. We have linked the wikipedia page for fine chemicals. The CNS agent has been changed to central nervous system to help explain what it is, however, the actual compound is no so important as the scale the reaction is run on to obtain the compound. The mechanism for coupling two double bonds has been changed to explain the steps better. We have cleared up typos, as far as we know, and rewrote sections to remove awkward phrasing.Organic Chemist 19 (talk)

ajc540

Thanks for your review! Here is what we have edited and worked on: We have reworded the introduction to remove redundancy and cleared up sentences to be more concise. I liked your point about the base and that it should be included in the introduction. The reaction mechanism has been edited to eliminate conflicting information such as the rate limiting step. We have removed the ranking of metals in the section because we agree it did not fit in that section. The kinetics section was removed and added to other parts of the mechanism section. We also included the stereochemistry discussion in with the other sections because we talk about the cis-tran isomerization of the palladium complex and that example seemed to fit well there. Breaking the applications section into two different sections was a good suggestion and we did that for the article. The variations section was edited, along with the addition of schemes, to help explain this section better for the general reader. We left much of the information in there but hopefully breaking it apart and adding schemes will help this section be more wikipedia-ish. We believe we removed some sections int he variations that were not so relevant and reworded sections in the hope that they would make more sense. The advantages section was placed before the application section and provides better flow for the article. The figures have been labeled better with names of molecules where relevant and drawn to all look the same and the same size.Organic Chemist 19 (talk)

UMChemProfessor

Thanks for your review! Here is what we have edited and worked on: We have moved more specific information that was previously included in the introduction to later sections of the article. We have merged the kinetics section with the rest of the reaction mechanism section. The advantages section has been moved to flow better with the article. This section was not deleted because we believe there are many advantages that can me noted for the reaction and that all of them would not fit nicely into other sections of the article. We tried to remove any talk of advantages from the rest of the article and include them here to make it a more significant section as well. We have made our diagrams all the same format and the same size.Organic Chemist 19 (talk)

ChemLibrarian

Thanks for your review! Here is what we have edited and worked on: We have made all of the images the same format and uploaded all of the to wikimedia commons first. We have changed the format on incorrect references, as far as we know. There may be some references that we did not add that we could have missed and could still be incorrect, hopefully not. Signatures have been deleted.Organic Chemist 19 (talk)

Iterative SM coupling

Hi, it is a bit surprising at the lack of mention of or relevant references to iterative cross coupling procedures using MIDA boronates. The former can be used to synthesise around >95% of all polyene backbones in natural products.

Also, Gregory Fu has done a lot of work in generalising the condition for C(sp3)-C(sp3) coupling, yet, this major advancement which enables direct C-C formation between primary moieties is vaguely mentioned once in the text with a single reference.

Yogiholt (talk) 05:34, 9 April 2015 (UTC)

References

Query

In industrial applications, surely these are boronic acids, not boranes? — Preceding unsigned comment added by 212.159.47.23 (talk) 12:25, 29 March 2017 (UTC)

Chem Abs report

Reasons for WP:SECONDARY and WP:TERTIARY: "2237 references were found containing "Suzuki reaction" as entered. 22094 references were found containing the concept "Suzuki reaction"." --Smokefoot (talk) 11:38, 28 June 2018 (UTC)