Talk:Sonogashira coupling

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To Shwinn Ricci:

I'm glad to see more work being put into this article! I think you are new around here, welcome! Some constructive feedback on this article:

1. Many of the jpg files you have uploaded are pretty clearly taken from manuscripts directly, I'm pretty sure this is not okay and will get your images justifiably deleted. The ORTEP is clearly not your original work unless you got the cif file and made it yourself. You need to re-draw them in chemdraw, then convert them to svg (preferred) or png (okay if svg give you trouble). When you upload your own images, you must use the least restrictive license or it will be flagged.
2. Your chemdraw images seem to be using the (terrible) default Chemdraw settings. Be sure to choose "File->Open Stationary->ACS 1996" so that you have reasonable bond lengths and font sizes.
3. As mentioned above, references should conform to Wikipedia guidelines and include doi numbers for linking.
4. I feel that a lot of the recent edits are hap-hazard and distracting. There are thousands of pages on the Sonogashira coupling reaction, this article should distill the important, general information into a readable, concise, clear document. More ≠ better. Think short, critical Angew. Chem. review, not long Chem. Rev.Dweix (talk) 03:02, 16 December 2011 (UTC)

• the crystal structure should go but as it does not have a proper licence it will eventually be deleted. V8rik (talk) 23:15, 16 December 2011 (UTC)

Trans-cis isomerization in the figure doesn't actually happen in the structure shown (Step D essentially does "nothing" as shown)

Should the R3NH2+ in the copper catallytic cycle not be R3NH+? — Preceding unsigned comment added by Eggilicious (talk • contribs) 12:04, 22 February 2012 (UTC)

• Yes, I can confirm the error exists. Edit made [http://en.wikipedia.org/w/index.php?title=Sonogashira_coupling&action=historysubmit&diff=252773624&oldid=250589825 here]. We could fall back to the one that already existed V8rik (talk) 16:43, 22 February 2012 (UTC)

Hi,

Recently, I have found some article that concerns synthesis of disubstituted ethynes by nonclassical Sonogashira reaction. This variant allows to use TMS protected alkynes (this kind of protecting group is not reactive in classic Sonogashira reaction), and it's free of amine usage. Ratio of Palladium catalyst to Copper(I) Chloride is crucial, and CuCl is added in molar quantities to substrates. This method allows to obtain symetrical and unsymetrical disubstitued alkynes in one reaction from aryl iodides and protected alkynes. I've tried this reaction a few times and yields were about ~70%.

Two examples of my own:

4-iodobenzonitrile + 1,4-bis(trimethylsilyl)-1,3-butadiyne ----> 4,4'-(buta-1,3-diyne-1,4-diyl)dibenzonitrile Y=75%

4-iodopyridine + 1,4-bis(trimethylsilyl)-1,3-butadiyne ----> 4,4'-(buta-1,3-diyne-1,4-diyl)dipyridine Y=82%

Here is the link to the article:

http://www.sciencedirect.com/science/article/pii/S0040402012004462

I think this method is worth of being mentioned in this article. English is not my first language, so I don't want to take this responsibility and add any content to this article.

Best regards,

A Leniak (talk) 22:22, 5 March 2015 (UTC)

=A major edit to update and repack the contents (Dec 2018)=

Hello,

I have decided to reconfigure the current design of the "Sonogashira coupling" wiki article, as to implement and update the latest discoveries in the field. Also some of the topics were repeated throughout the text and required reorganization in a more concise fashion.

Thus, the initial reaction scheme was changed to a colourized one to follow the colour theme through the whole document. It is also in the ACS style rather than a simple equation form.

The History section was updated to emphasize the reason why the alkynylations are termed "Sonogashira", despite using the original Pd/Cu catalytic systems. In that view, copper-free Sonogashira reaction could be as well entitled as the Cassar-Heck alkynylation.

Mechanism The mechanism scheme was generalized. Also the colour code was slightly modified to emphasize the origins of alkyl group. Cis-trans isomerization from former C to D was removed from the scheme since it is not exactly true for all the catalysts types (some bidentate ligands prevent the formation of trans-OA). The process is now just mentioned in the discussion.

The end paragraph, discussing the different active catalytic species was incorporated into the "Pd cycle" discussion, since it is a crucial part in the OA formation – not all are formed in the previously depicted trans geometry and it is more correct to display it as LnPd-ArX.

Since the mechanism of the Cu-free reaction was recently discovered, it was included as a subtitle in this section.

Prior mechanistic discussion was removed from The Copper-free Sonogashira reaction section under Reaction variations. The contents were modified to just describe the reasons, benefits and drawbacks of this alternative coupling procedure.

Arenediazonium precursors section was moved from Catalyst variation to the Reaction conditions. Au/Pd is still mentioned under Catalyst variation and thus repeating of the topic is avoided.

Reaction conditions – sub-titles were introduced, namely Catalysts; Aryl halides and pseudohalides; Alkynes; and Bases.

Best regards,

Miha (talk) 13 December