Transition Metal-Catalyzed Couplings

Transition metal-catalyzed cross-coupling reactions have gained widespread use in both academic and industrial laboratories as a powerful methodology for the formation of C-C and C-heteroatom bonds, and have subsequently become an indispensable tool in modern organic synthesis.

Reactions using transition metal catalysts have a rich history that has led to the awarding of the 2010 Nobel Prize in Chemistry jointly to Professors Suzuki, Heck, and Negishi for their pioneering contributions in this field.

One of the earliest named reactions in this category was discovered in 1901 by F. Ullmann when he combined two equivalents of an aryl halide with one of powdered copper at a high temperature and generated the equivalent biaryl compound. Subsequently, the Ullmann reaction has become a convenient method to create numerous biaryl compounds.

• Heck reaction
• Negishi cross-coupling reaction
• Stille cross-coupling reaction
• Suzuki cross-coupling reaction
• Ullmann reaction

• Buchwald-Hartwig coupling
• Castro-Stevens coupling
• Glaser coupling
• Kumada cross-coupling
• Larock indole synthesis
• Miyaura boration
• Sonagashira cross-coupling