Benzyne Route in Aromatic Substitution

Benzyne can drive nucleophilic aromatic substitution when simple aryl halides are exposed to strong base or high heat. In this pathway, the ring does not react by the usual route. Instead, it forms a very reactive intermediate called benzyne.

The mechanism begins with a strong base removing a pro...

Unactivated halobenzenes typically do not react with nucleophiles. However, the reaction can occur under forced conditions such as using high temperatures and high pressures, or strong bases.

An isotopic labeling experiment indicates that the reaction produces two products in roughly equal amounts.

The reaction involves a benzyne i...