Iron-catalyzed oxidative C–C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air. Issue 33 (4th April 2019)

• Record Type: Journal Article
• Authors: Liu, Binbin; Cheng, Lu; Hu, Penghui; Xu, Fangning; Li, Dan; Gu, Wei-Jin; Han, Wei
• Is Part Of: Chemical communications. Volume 55:Issue 33(2019)
• Page Start: 4817
• Page End: 4820
• Publication Date: 2019-04-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc01995b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The iron-catalyzed C−C single bond cleavage and oxidation of allylarenes without the assistance of heteroatoms/directing groups to produce aryl aldehydes is disclosed. Abstract : A general and selective iron-catalyzed allylic C–C(vinyl) σ-bond cleavage of allylarenes without the assistance of heteroatoms to give aryl aldehydes is reported. The unstrained carbon–carbon single bond cleavage reaction uses ambient air as the sole oxidant, proceeds efficiently at room temperature, and allows for exceptional functional-group tolerance, which addresses the long-standing challenges of current C–C bond cleavage/functionalization. Notably, the method enables rapid late-stage oxidation of complex bioactive molecules and can be used to expedite syntheses of natural products (vanillin and glucovanillin) from readily available chemical feedstocks.