State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
Molecules. 2022 Jun 23;27(13):4047. doi: 10.3390/molecules27134047.
Near-infrared (NIR) light-triggered photoredox catalysis is highly desirable because NIR light occupies almost 50% of solar energy and possesses excellent penetrating power in various media. Herein we utilize a metal-free boron dipyrromethene (BODIPY) derivative as the photocatalyst to achieve NIR light (720 nm LED)-driven oxidation of benzylamine derivatives, sulfides, and aryl boronic acids. Compared to blue light-driven photooxidation using Ru(bpy)Cl as a photocatalyst, NIR light-driven photooxidation exhibited solvent independence and superior performance in large-volume (20 mL) reaction, presumably thanks to the neutral structure of a BODIPY photocatalyst and the deeper penetration depth of NIR light. We further demonstrate the application of this metal-free NIR photooxidation to prodrug activation and combination with Cu-catalysis for cross coupling reaction, exhibiting the potential of metal-free NIR photooxidation as a toolbox for organic synthesis and drug development.
近红外（NIR）光引发的光氧化还原催化是非常可取的，因为近红外光占据了太阳能的近 50%，并且在各种介质中具有出色的穿透能力。在此，我们利用一种无金属的硼二吡咯甲川（BODIPY）衍生物作为光催化剂，实现了 NIR 光（720nm LED）驱动的苄胺衍生物、硫化物和芳基硼酸的氧化。与使用 Ru(bpy)Cl 作为光催化剂的蓝光驱动的光氧化相比，NIR 光驱动的光氧化表现出溶剂独立性和在大体积（20mL）反应中的优异性能，这可能归因于 BODIPY 光催化剂的中性结构和 NIR 光的更深穿透深度。我们进一步展示了这种无金属的 NIR 光氧化在前药激活和与 Cu 催化的交叉偶联反应中的应用，展示了无金属的 NIR 光氧化作为有机合成和药物开发工具包的潜力。
