Question

Draw the two constitutionally isomeric structures formed when iodobenzene and propene are subjected to the conditions...

Draw the two constitutionally isomeric structures

Draw the two constitutionally isomeric structures formed when iodobenzene and propene are subjected to the conditions of the Heck reaction. If stereoisomers are possible for a particular constitutional isomer, draw the more stable stereoisomer.

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Concepts and reason

Coupling reaction: Two substrates that are combined in the presence of a metal catalyst is known as coupling reaction. In these reactions, normally substrates are activated using a base, which is useful to the insertion metal catalyst.

Fundamentals

Heck coupling reaction: Coupling reaction occurs between activated alkene, and the vinyl halide or aryl halide is called as the Heck coupling reaction. In this reaction, a small amount of base is used to activate boric acid.

X
R
Pd-cat
+
base

Given reaction condition is drawn below.

Pd(OAc) catalyst
dimethyl formamide
15h 100°C

In the above reaction Pd(PPh3)4{\rm{Pd}}{\left( {{\rm{PP}}{{\rm{h}}_{\rm{3}}}} \right)_{\rm{4}}} reagent was used, which is useful in coupling reactions. Given two substrates are best adoptable for Heck coupling reactions because one substrate is boric acid derivative, while the other is an alkenyl halide derivative.

Given reaction condition is drawn below.

Product of the given reaction (Heck coupling) is drawn below in products side.

Pd(OAc)2catalyst
dimethyl formamide
15h 100°C
major

Ans:

Pd(OAc)2catalyst
dimethyl formamide
15h 100°C
major

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