期刊
ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 24, 页码 6958-6967出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01441f
关键词
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资金
- FWO [11H0121N]
- VLIR-UOS [CU2018TEA458A101]
- RUDN University Strategic Academic Leadership Program
- CITMA [PN223LH010-002]
- NLHPC, Chile [ECM-02]
The visible-light promoted photoredox-cobalt catalyzed Minisci reaction allows for mild cross-coupling reactions using various boronic acids and derivatives as alkyl radical precursors. This reaction has high efficiency, good selectivity, and broad applicability for different N-heteroarenes.
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 center dot h(-1) in flow vs. 0.02 mmol center dot 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.
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