Jinyu Tang, Xi Zhao, Jinxuan Ni, Yanping Huo, Yang Gao, Xianwei Li, Yan Liu, Keiji Maruoka, Qian Chen
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引用次数: 0
Abstract
The development of the C–C bond cleavage of allylarenes is of vital importance. However, the cleavage of C(sp3)–C(sp2) σ-bonds has been rarely reported previously. Herein, we disclose an efficient and green photooxidative cleavage of C(sp3)–C(sp2) σ-bonds of allylarenes under the irradiation of blue LEDs using anthraquinone (AQ) as the photocatalyst and eco-friendly molecular oxygen (O2) as the sole oxidant. The newly developed reaction shows broad substrate scopes under metal- and additive-free conditions, providing practical and scalable access to aromatic aldehydes and ketones. Preliminary mechanistic studies suggest that a delocalized allylic radical generated via a hydrogen atom transfer (HAT) between photoexcited AQ (AQ*) and the allylic C(sp3)–H bond might be involved in this transformation.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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