The merger of photoredox catalysis and organometallic chemistry has effectively enabled multiple cross-coupling pathways. Here we report a visible-light promoted photoredox-cobalt catalyzed Minisci reaction of N-heteroarenes under mild conditions, employing various boronic acids and derivatives as alkyl radical precursors. This study demonstrates the prominent ability of the Co co-catalyst to promote the oxidation step of the photocatalytic cycle following a reductive quenching pathway, thus avoiding the use of stoichiometric (inorganic) oxidants. This feature enables the straightforward application of photo-flow conditions, particularly attractive for an easy scale-up and to enhance the efficiency of the reaction (throughput: 0.78 mmol·h⁻¹ in flow vs. 0.02 mmol·h⁻¹ in batch). Furthermore, the process is predominantly selective towards the C2-alkylation of quinolines and a mechanistic rationale has been provided with both experimental and DFT calculation support. The developed protocol demonstrates broad applicability for the alkylation of different N-heteroarenes under suitable homogeneous conditions for a flow-compatible Minisci reaction.

中文翻译：

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合并双重光氧化还原/钴催化和硼酸（衍生物）活化以进行 Minisci 反应

光氧化还原催化和有机金属化学的结合有效地实现了多种交叉偶联途径。在这里，我们报告了在温和条件下可见光促进的N-杂芳烃的光氧化还原-钴催化 Minisci 反应，使用各种硼酸和衍生物作为烷基自由基前体。该研究证明了 Co 助催化剂在还原猝灭途径后促进光催化循环氧化步骤的显着能力，从而避免使用化学计量（无机）氧化剂。此功能使光流条件的直接应用成为可能，对于轻松放大和提高反应效率特别有吸引力（吞吐量：0.78 mmol·h ^-1流量vs.0.02 mmol·h ^-1批次）。此外，该过程主要对喹啉的 C2-烷基化具有选择性，并且已经提供了实验和 DFT 计算支持的机械原理。所开发的协议证明了在适合流动兼容的 Minisci 反应的均相条件下对不同N-杂芳烃进行烷基化的广泛适用性。