The identity of a heteroatom within an aromatic ring influences the chemical properties of that heterocyclic compound. Systematically evaluating the effect of a single atom, however, poses synthetic challenges, primarily as a result of thermodynamic mismatches in atomic exchange processes. We present a photocatalytic strategy that swaps an oxygen atom of furan with a nitrogen group, directly converting the furan into a pyrrole analog in a single intermolecular reaction. High compatibility was observed with various furan derivatives and nitrogen nucleophiles commonly used in drug discovery, and the late-stage functionalization furnished otherwise difficult-to-access pyrroles from naturally occurring furans of high molecular complexity. Mechanistic analysis suggested that polarity inversion through single electron transfer initiates the redox-neutral atom exchange processes at room temperature.

中文翻译：

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光催化呋喃制吡咯转化


芳香环内杂原子的身份会影响该杂环化合物的化学性质。然而，系统地评估单个原子的影响会带来合成挑战，主要是由于原子交换过程中的热力学失配。我们提出了一种光催化策略，将呋喃的氧原子与氮基交换，在单个分子间反应中直接将呋喃转化为吡咯类似物。观察到与药物发现中常用的各种呋喃衍生物和亲氮试剂高度相容，并且后期官能团化提供了来自高分子复杂性的天然呋喃的难以获得的吡咯。机理分析表明，通过单电子转移进行的极性反转在室温下启动了氧化还原中性原子交换过程。