Visible‐Light‐Promoted Efficient Aerobic Dehydrogenation of N‐Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions. Issue 13 (17th March 2020)

• Record Type: Journal Article
• Authors: Yu, Kunyi; Zhang, Hanjie; Su, Chenliang; Zhu, Yongfa
• Is Part Of: European journal of organic chemistry. Issue 13(2020)
• Page Start: 1956
• Page End: 1960
• Publication Date: 2020-03-17
• Subjects: Aerobic dehydrogenation -- Nitrogen heterocycles -- Perylene diimide -- Organic semiconductors -- Photocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000170
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N‐heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high‐efficiency photo‐oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N‐heteroarenes, gram‐scale experiments as well as reusability tests. Abstract : Aerobic dehydrogenation of N‐heterocycles into quinolines, indoles, benzimidazoles, benzothiazoles, and benzoxazoles is achieved by a reusable organic semiconductor photocatalytic system under ambient conditions. Spectral data and quenching experiments are used to explain the aggregation state of the catalyst and the photo‐oxidation mechanism.