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<p>(Hetero)polyaryl amines are extensively prevalent in pharmaceuticals, fine chemicals, and materials but the intricate and varied nature of their structures severely restricts their synthesis. Here, we present a selective multicomponent cycloaromatization of structurally and functionally diverse amine substrates for the general and modular synthesis of (hetero)polyaryl amines through copper(I)-catalysis. This strategy directly constructs a remarkable range of amino group-functionalized (hetero)polyaryl frameworks (194 examples), including naphthalene, binaphthalene, phenanthren, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, quinoline, isoquinoline, quinazoline, and others, which are challenging or impossible to obtain using alternative methods. Copper(III)-acetylide species are involved in driving the exclusive 7-<i>endo</i>-<i>dig</i> cyclization, suppressing many side-reactions that are susceptible to occur. Due to the easy introduction of various functional units into heteropolyarylamines, multiple functionalized fluorescent dyes can be arbitrarily synthesized, which can serve as effective fluorescent probes for monitoring the pathological processes (e.g. chemotherapy-induced cell apoptosis) and studying the related disease mechanisms.</p>

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General (hetero)polyaryl amine synthesis via multicomponent cycloaromatization of amines

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年1月2日

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  • Lebin Su,
  • Jianyu Dong,
  • Yang Shen,
  • Shimin Xie,
  • Shaofeng Wu,
  • Neng Pan,
  • Feng Liu,
  • Qian Shang,
  • Fangfang Cai,
  • Tian-Bing Ren,
  • Lin Yuan,
  • Shuang-Feng Yin,
  • Li-Biao Han,
  • Yongbo Zhou

摘要

(Hetero)polyaryl amines are extensively prevalent in pharmaceuticals, fine chemicals, and materials but the intricate and varied nature of their structures severely restricts their synthesis. Here, we present a selective multicomponent cycloaromatization of structurally and functionally diverse amine substrates for the general and modular synthesis of (hetero)polyaryl amines through copper(I)-catalysis. This strategy directly constructs a remarkable range of amino group-functionalized (hetero)polyaryl frameworks (194 examples), including naphthalene, binaphthalene, phenanthren, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, quinoline, isoquinoline, quinazoline, and others, which are challenging or impossible to obtain using alternative methods. Copper(III)-acetylide species are involved in driving the exclusive 7-endo-dig cyclization, suppressing many side-reactions that are susceptible to occur. Due to the easy introduction of various functional units into heteropolyarylamines, multiple functionalized fluorescent dyes can be arbitrarily synthesized, which can serve as effective fluorescent probes for monitoring the pathological processes (e.g. chemotherapy-induced cell apoptosis) and studying the related disease mechanisms.