Cadiot–Chodkiewicz coupling
Cadiot–Chodkiewicz coupling is an organic chemistry reaction that forms a carbon-carbon bond between two different alkynes, one of which must possess a leaving group, typically a halide. This reaction is a valuable tool in the synthesis of conjugated enynes and polyynes, compounds that are of significant interest due to their electronic properties and potential applications in materials science and pharmaceuticals. The Cadiot–Chodkiewicz coupling is named after the French chemist Pierre Cadiot and the Polish chemist Wladyslaw Chodkiewicz, who developed the reaction.
Mechanism[edit | edit source]
The Cadiot–Chodkiewicz coupling mechanism involves a copper(I) catalyst, often CuCl or a Cu(I) acetylide complex. The reaction proceeds through the formation of a copper acetylide by the reaction of the copper(I) salt with the terminal alkyne that has a hydrogen atom. This copper acetylide then reacts with the alkyne that has a leaving group (usually a halide) to form a new carbon-carbon bond, resulting in the formation of a conjugated diyne. The process is an example of a homocoupling reaction, although it couples two different alkynes.
Applications[edit | edit source]
The Cadiot–Chodkiewicz coupling has been applied in the synthesis of complex natural products and in the construction of molecules for materials science, including organic conductors and liquid crystals. Its ability to selectively form conjugated enynes and polyynes makes it a powerful tool in the synthesis of compounds with specific electronic properties.
Advantages and Limitations[edit | edit source]
One of the main advantages of the Cadiot–Chodkiewicz coupling is its ability to form conjugated systems without the need for pre-functionalization of the alkyne substrates, which can be a limitation in other coupling reactions such as the Sonogashira coupling. However, the reaction's efficiency can be affected by the nature of the substituents on the alkynes, and the need for a copper catalyst can limit its applicability in certain contexts, especially in the presence of sensitive functional groups.
See Also[edit | edit source]
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
|
WikiMD's Wellness Encyclopedia |
| Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD
