Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a new $\text{C-C}$ bond. In Suzuki coupling reaction, a vinylic or aryl halide $\text{R-X}$ is treated with an organometallic compound $\text{R’-B}{\left(\text{OR”}\right)}_{\text{2}}$ and a palladium catalyst $\left(\text{PdLn}\right)$ under basic conditions. Suzuki reaction is stereospecific involving possible $\text{E/Z}$ isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If $\text{R-X}$ halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If $\text{H-R’}$ is vinylic and has an attached substituent at the opposite end of the $\text{C=C}$, then $\text{R}$ and the substituent will be trans to each other in the product.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a new $\text{C-C}$ bond. In Suzuki coupling reaction, a vinylic or aryl halide $\text{R-X}$ is treated with an organometallic compound $\text{R’-B}{\left(\text{OR”}\right)}_{\text{2}}$ and a palladium catalyst $\left(\text{PdLn}\right)$ under basic conditions. Suzuki reaction is stereospecific involving possible $\text{E/Z}$ isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If $\text{R-X}$ halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If $\text{H-R’}$ is vinylic and has an attached substituent at the opposite end of the $\text{C=C}$, then $\text{R}$ and the substituent will be trans to each other in the product.