Question

Suzuki coupling of aryl iodide A and vinyl borane B affords compound C, which is converted to D in the presence of aqueous acid. Identify compounds C and D and draw a stepwise mechanism for the conversion of C to D.

Short answer

Answer

Step-by-step solution

Suzuki Coupling

The cross-coupling reaction involving the synthesis of polyolefins and styrene from boronic acid reacting with an organohalide in the presence of the palladium (0) complex is referred to as the Suzuki Coupling reaction.

Formation of C by the Suzuki coupling of the organoborane and aryl halide.

Formation of D

The compound C is acid hydrolyzed to form a new C-N bond. The deprotonation from the nitrogen atom is followed by the abstraction of proton by oxygen atom. The protonated ion is stabilized by the removal of ethanol and removal of hydrogen to form C=C bond which would yield the required compound D.

Formation of D from C