Question

Devise a synthesis of diene A from (Z)-2-bromostyrene as the only organic starting material. Use a Suzuki reaction in one step of the synthesis.

Short answer

Answer

Synthesis of compound A

Step-by-step solution

Coupling reactions

Reactions in which two hydrocarbon fragments are coupled in the presence of a catalyst are called coupled reactions.

The catalysts used are metals like palladium, cobalt, and other metal or metal complexes.

The reaction is mainly used to form new C-C sigma bonds.

Suzuki reaction

Suzuki reaction is a coupling reaction that involves an organoborane catalyst that reacts in the presence of a metal catalyst. It forms an adduct that couples with another halide to form the product.

Suzuki reactions are mainly used to couple sp² hybridized carbon atoms or unsaturated compounds.

It is used to synthesis bi aryl motifs used in drug delivery.

Mechanism of the given reaction

2-bromo styrene reacts with sodium nitrile to form phenylethyne, which reacts with an organoborane catalyst to form an adduct. This adduct reacts with another 2-bromostyrene molecule in the presence of metal to form the final product A.

Synthesis of compound A