Photoredox Cleavage of a Csp3–Csp3 Bond in Aromatic Hydrocarbons
- Ke LiaoKe LiaoState Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, ChinaMore by Ke Liao
- Cho Ying ChanCho Ying ChanDepartment of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong KongMore by Cho Ying Chan
- Siqi LiuSiqi LiuPingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen 518118, ChinaMore by Siqi Liu
- Xinhao ZhangXinhao ZhangState Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, ChinaPingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen 518118, ChinaMore by Xinhao Zhang
- Jiean Chen*
- , and
- Yong Huang*
Functionalizing molecules through the selective cleavage of carbon–carbon bonds is an attractive approach in synthetic chemistry. Despite recent advances in both transition-metal catalysis and radical chemistry, the selective cleavage of inert Csp3–Csp3 bonds in hydrocarbon feedstocks remains challenging. Examples reported in the literature typically involve substrates containing redox functional groups or highly strained molecules. In this article, we present a straightforward protocol for the cleavage and functionalization of Csp3–Csp3 bonds in alkylbenzenes using photoredox catalysis. Our method employs two distinct bond scission pathways. For substrates with tertiary benzylic substituents, a carbocation-coupled electron transfer mechanism is prevalent. For substrates with primary or secondary benzylic substituents, a triple single-electron oxidation cascade is applicable. Our strategy offers a practical means of cleaving inert Csp3–Csp3 bonds in molecules without any heteroatoms, resulting in primary, secondary, tertiary, and benzylic radical species.
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