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Page created as course work under Education Program[edit]

Hello, we are working on this page for an advanced chemistry course under the Wikipedia Education Program. More content to be added in the next couple of days. Please do not delete this part as a stub. Thank you! ChemLibrarian (talk) 02:33, 11 November 2013 (UTC)

Peer review[edit]

The introductory section has a lot of good information but a non-expert may be confused by the wording. After rereading I am starting to understand what is being states. Defining organoboron reagents briefly (more than just the hyperlink and the figure) will allow for an easier read. Furthermore, “Metal-catalyzed C-H borylation reactions are a target research area for the synthesis of organoboron compounds, having the advantages of one step synthesis from simple organic molecules, use of mild temperatures and reagents, and high selectivity” should be broken into two sentences.

The aliphatic C-H borylation section seems very brief for it to have its own subheading. I would suggest either expanding upon this topic or figuring how to incorporate it into another section(s). The named reaction section of the page does highlight the uses of borylation and is a very good summary of these reactions. I feel it would make your page stronger if you included what was novel about each of these reactions, more than just stating what the parameters are for each reaction.

All of the reactions named have their own wiki page and should be linked in some sort of fashion. I would be cautious about the amount of detail provided for these reactions in your wiki page. The majority of your wiki page is these names reactions. Is there a way to focus more on the applications of the product synthesized than the reactions itself? This approach seems to have less repetition of the already established Wikipedia pages.

Also, a lot of the chemists mentioned also have their own wiki pages that should be linked with their name. The only other one that I recommend is to link hybridization when you are talking about sp2 hybridization of the boron atom. You have linked most of the concepts already, which makes it easy to navigate and understand the page.

The figures are really well drawn. I can tell that a lot of effort was put into these schemes. I would, however, bold them in ChemDraw before saving them to make them easier to read. In the reaction section it I difficult to find the figures that go with the reaction since they are off centered. I think that the thumbnails make it very confusing as a reader to follow the content. Furthermore, is it necessary to have two figures for one reaction? If so, please explain the significance of each in the paragraphs and provide a more comprehensive caption.

There are a lot of citations for the wiki page, however, a lot of the articles are primary sources. Are there sources you could cite that have an overview of borylations i.e. organic chemistry textbooks, or a review summarizing all the borylation reactions. I know some of these were used in the beginning but near the end there were quite a few primary sources. The other thing I am unsure of is the red labels reading “extra pages.” What is that referring to and is it something that needs to be addressed?

Overall the wiki page is very well written. There is on minor error I found was BH3THF should be BH3THF. The page explains reactions that borylation is used. I am just a bit confused as to where the physical organic chemistry comes to play. You mention the characteristic of the C-B bond and compare it to a C-C bond but do not explain the significance of the difference. Furthermore you mention that borylation occurs at the least sterically hindered site but never explain the phys org behind the statement. I think incorporating the physical organic aspects of borylation and focusing less on the named reaction will make your page stronger and more useful to chemistry.

(Physorgchem13 (talk) 20:44, 29 October 2013 (UTC))

Peer review[edit]

Some of the terminology in the introduction may be difficult for a non-expert to understand without further explanation. For example the first sentence could be supplemented with a link or an explanation when you mention the functionalization of aliphatic C-H bonds; providing a "pipe" link such as aliphatic C-H bonds would make the terminology clear. The statement mentioning the "broad applications" of organoboranes in material science seems vague. Clarifying this statement (i.e. if you mean they are used as synthetic precursors for materials synthesis) or providing specific examples of applications where organoboranes are used as materials may help. Also, when you mention Bis(pinacolato)diboron I think it may help to include "(Bpin)" after the name since you begin to refer to Bpin in later sections without stating what it is.

The second section should have a link to Lewis Acid since it provides important information for understanding the concept. Also, since in borylation involves functionalizing a C-H bond it may be appropriate to compare the C-B bond to a C-H bond as well. The sections titled Aliphatic borylation and Aromatic Borylation should be combined into one since the lengths are not appropriate for each to have a separate section. However, since the main topic of this page is borylation, and it appears to focus on metal catalyzed borylation, I think you should go more in depth on these subjects. Also, for the C-H borylation of functionalized non-aromatic hydrocarbons there is a dependance on electronic effects that may be worth noting (see your reference # 8). I found a dissertation (2013) on irridium catalyzed borylation of aliphatic and aromatic C-H bonds from one of Dr. John Hartwig's students here (just download the pdf on the linked page) which provides a mechanism (pg 67 and up) plus a lot of sources and information on the subject. I think going into more depth on these topics would allow you to connect C-H borylation to relevant concepts in physical organic chemistry. For the aromatic C-H borylation section I think including an example reaction of the 1,3-substituted arene, in place of the 1,2-isomer, would be more appropriate since it would illustrate the steric effect rather than just mentioning it. Also, explaining what type of electronic effects (and illustrating how) are responsible for directing the aromatic C-H borylation sites would be helpful.

The section concerning applications of Organoboranes gives a lot of synthetic examples but it may be more appropriate for the [Organoborane] wikipedia page since it is not directly related to C-H borylation and fits nicely with some of the content on the organoborane page. Also, I would recommend to make the figures larger and positioning them under their corresponding sub-section. For example when inserting an image, "[[File:file name|thumb|400px|center|Figure Description]]", the 400px gives the size of the figure, the number can be varied to give appropriate size, and the "center" gives the positioning (you can modify with "left" and "right" as well).

Overall, the page could be improved upon in the following ways: provide links or brief explanations to terms or concepts that is not considered common knowledge for your target audience, going into greater depth on aliphatic and aromatic C-H borylation, attempting to make connections with relevant physical organic chemistry concepts and organizing/formatting figures in the synthetic applications section. The page seems to focus on synthetic applications of organoboranes and I strongly feel that the section concerning C-H borylation could be expanded upon (which should open up connections to phys. org chem. concepts ((i.e. electronic effects, non-covalent interactions, strain...)). The page does a good job highlighting the importance of organoboranes in synthesis and characterizing the C-B bond. The information about aromatic C-H borylation was concise (which is ideal for wikipedia pages) and overall the page provided several useful examples to illustrate important points. Charco0917 (talk) 23:29, 2 November 2013 (UTC)

Suggestions from ChemLibrarian (talk) 03:25, 5 November 2013 (UTC)[edit]

  1. You added nice images but all of them are in thumbnail. For some places it's good but for most paragraphs, you probably want to enlarge the picture and place them at the center of the page so that people can read them without clicking on them and the whole page can flow better too. See this page Wikipedia:Picture tutorial for how to place the image at different places and adjust the size. Other reviewers gave good input about this too.
  2. You have some errors with your references. I noticed that mostly it's because you have both the page number and page counts. For example, you can fix reference 12 by changing "...|volume=109|page=7925|pages=2|doi=10.1021/ja00259a075..." to "...|volume=109|page=7925-7927|doi=10.1021/ja00259a075..."
  3. You do not need to title the first paragraph as Introduction. Just delete the heading "Introduction". People usually know the first paragraph is an overview of the concept.
  4. Please make the capitalization of your headings consistent. Usually, we do not need the words all capitalized.

Additional Comments[edit]

UMChemProfessor (talk) 19:57, 5 November 2013 (UTC) I agree with most of the peer reviewer comments and those of Ye Li. You did a fantastic job pulling a variety of different concepts together into a unified "overview" of C-H borylation. It's a great article and just needs some minor improvements, as noted above.

Response to Peer Reviews[edit]

Dear Reviewers,

Thank you very much for your reviews on our group’s web page. According to the helpful suggestions of the three reviewers, we have made several corrections for our webpage.

1. According to the three reviewers’ suggestions on our images, we have changed the positions and sizes of them. Now these pictures are placed in the middle of the web page and several of them are enlarged to a proper size.
2. According to the reviews about our references, we have corrected several mistakes in the references and also added some reviews to references of the application section.
3. According to the suggestions from ChemLibrarian, we have deleted the tilte of the first paragraph.
4. According to the suggestions from ChemLibrarian, we have made the capitalization of our headings consistent and deleted the all capitalized words.
5. According to the suggestions from Physorgchem13 and Charco0917, we have added some examples of the application of these named reactions in the total synthesis of natural products.
6. According to the suggestions from Physorgchem13 and Charco0917, we have added several links to our pages and also added the ‘see also’ section to link the related pages to our web page. Any reactions and chemists that have their own Wikipedia page has been linked through our page, as suggested by Physorgchem13. Additionally, hybridization was linked when discussing the sp2 hybridization of the boron atom.
7. Physorgchem13 suggested that we defined organoboron reagents, so we defined organoboron reagents in the opening sentence as organic compounds containing a carbon-boron bond.
8. Rewording the introduction was suggested by both Physorgchem13 and Charco0917. We removed the sentence “Metal-catalyzed C-H borylation reactions are a target research area for the synthesis of organoboron compounds…” and rewrote it so the importance of metal-catalyzed C-H borylation reactions is described more clearly over a few sentences.
9. We added information about the C-H bond compared to the C-B bond as suggested by Charco0917.
10. We expanded the section of aliphatic C-H borylation. Physorgchem13 suggested that we describe what is novel about this reaction. In this case, it is the selective functionalization of primary C-H bonds in alkanes which has been described in this section. We also added mechanistic details that incorporate physical organic concepts, such as steric effects, and mechanistic experiments, such as H/D exchange.
11. Charco0917 suggested that we explain what type of electronic effects are responsible for directing aromatic and aliphatic C-H borylation. For aliphatic borylation we included the fact that borylation occurs at the least electron rich primary carbon. Other electronic effects come into play when two different substrates are involved in the reaction, however, we felt this detail was beyond the scope of the Wikipedia article for the general population. For aromatic C-H borylation, these reactions are almost exclusively controlled by steric effects. In contrast, the C-H functionalization of heteroaromatic C-H bonds is controlled by electronic effects, so we expanded on this reaction as well.
12. As suggested by Physorgchem13 we included an example of 1,3-disubstited arenes, and how it compares to electrophilic aromatic substitution, to illustrate the steric effects of aromatic C-H borylation.
13. Mechanistic details were added for the C-H borylation of arenes. These details incorporate physical organic concepts as suggested by Charcho0917. We refrained from going into too much mechanistic detail in order to keep the article accessible for non-experts. Iriidium (talk) 13:23, 11 November 2013 (UTC)

DYK nomination[edit]

Writing for Wikipedia is difficult[edit]

Here are some alternative comments:

  1. Wikipedia is an encyclopedia, it is not a forum to host homework essays on their perception of the current literature.
  2. History shows us that students who are tasked with creating such essays are unlikely to ever edit again. What we have is a snapshot of the mostly primary literature that looks very good today, but what about its relevance in 5 years time? Who is going to tend this article? I guess one could say that an obsolete review is better than none. I would argue that it is possible to write content that is less time-senstive.
  3. According to Chemical Abstracts, somewhere between 1400 and 1000 papers and patents have appeared on borylation. On what basis were the 45 cited here (~4% of the total) selected? This consideration is the basis of WP:SECONDARY and WP:DISCRIMINATE.
  • Finally, the review does look nice, and what I am suggesting is difficult. --Smokefoot (talk) 01:05, 15 November 2013 (UTC)