Direct Synthesis of Polysubstituted Aldehydes via Visible‐Light Catalysis. Issue 8 (24th January 2018)

• Record Type: Journal Article
• Authors: Wu, Fengjin; Wang, Leifeng; Chen, Jiean; Nicewicz, David A.; Huang, Yong
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 8(2018)
• Page Start: 2174
• Page End: 2178
• Publication Date: 2018-01-24
• Subjects: aldehydes -- H-atom transfer -- photocatalysis -- radical cations -- styrene; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201712384
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Aldehydes are among the most versatile functional groups for synthetic chemistry. However, access to polysubstituted alkyl aldehydes is very limited and requires lengthy synthetic routes that involve multiple‐step functional‐group conversion. This paper reports a one‐step synthesis of polysubstituted aldehydes from readily available olefin substrates using visible‐light photoredox catalysis. Despite a number of competing reaction pathways, commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen‐atom‐transfer catalyst under blue LED irradiation. Alkyl aldehydes with different substitution patterns are prepared in good yields. This strategy can be applied to structurally sophisticated substrates. Abstract : Making light work : Commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen‐atom‐transfer catalyst under blue LED irradiation to provide polysubstituted aldehydes in one step. This strategy can be applied to structurally sophisticated substrates.