Nucleophilic aromatic substitution (SNAr) is a simple yet powerful method to construct a wide variety of aromatic architectures. The Katz group has shown that heteracalix[4]arene macrocycles are readily formed in a single step and in high yield by SNAr condensation of 1,3-diphenols, 1,3-diaminobenzenes, or 3-aminophenols with 1,3-dihalobenzenes bearing electron-withdrawing groups. The ability of acetylenes to activate fluorobenzenes for substitution by oxygen and nitrogen nucleophiles was recently reported by the Katz group. The scope and limitations of acetylene-activated SNAr reactions are discussed in the context of heteracalixarene and heterocycle synthesis.

Exploring acetylene-activated S<sub>N</sub>Ar reactions for heterocycle and macrocycle synthesis

248th National Meeting (2014)

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Exploring acetylene-activated SNAr reactions for heterocycle and macrocycle synthesis

Exploring acetylene-activated S_NAr reactions for heterocycle and macrocycle synthesis