It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we found that nucleophilic aromatic substitution requires strongly electron-withdrawing groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such products. As examples, write the products of the following reactions and state which coupling reaction is being utilized. Ph n-BugSn Pd(0), PPhg ÓTf excess Pd(PPH3)4, Cul, NE13

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It is typically very difficult to do a substitution reaction on an aromatic ring when the
leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we
found that nucleophilic aromatic substitution requires strongly electron-withdrawing
groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such
products. As examples, write the products of the following reactions and state which
coupling reaction is being utilized.
Ph
n-BugSn
Pd(0), PPhg
ÓTf
excess
Pd(PPH3)4, Cul, NE13
Transcribed Image Text:It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we found that nucleophilic aromatic substitution requires strongly electron-withdrawing groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such products. As examples, write the products of the following reactions and state which coupling reaction is being utilized. Ph n-BugSn Pd(0), PPhg ÓTf excess Pd(PPH3)4, Cul, NE13
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