Wheel of Aryl-aryl Coupling

In an aryl-aryl cross-coupling reaction, two different aryl fragments are joined.

Aryl-aryl cross-couplings, which are a subset of the more general coupling reactions, may involve carbon–carbon cross-coupling or carbon–heteroatom cross-coupling.

Cross-coupling reactions frequently require metal catalysts.

Wheel of aryl-aryl coupling: Click/tap to enlarge the image

Name reactions on the infographic:

• Pschorr (intramolecular coupling)
• Graebe-Ullmann (intramolecular coupling)
• Ullmann (homo coupling)
• Gomberg-Bachmann
• Wittig (via benzyne mechanism)
• Kumada
• Negishi
• Stille
• Suzuki-Miyaura
• Hiyama
• Hiyama-Denmark
• Buchwald-Hartwig (carbon–heteroatom cross-coupling)
• Chan-Evans-Lam (carbon–heteroatom cross-coupling)
• Liebeskind-Srogl

What other wheel(s) 🛞 of organic reactions would you like to see ❓Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Roman A. Valiulin, ChemInfoGraphic. ChemInfoGraphic. https://cheminfographic.wordpress.com.

(2)    Brown, C.; Ford, M. Higher Level Chemistry, 2nd ed.; Pearson Education: Harlow, Essex, 2014.

(3)    Ncert. Chemistry : Textbook for Class XI - Part.II; National Council Of Educational Research And Training: New Delhi.

(4)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.