Olefination of Alkyl Halides with Aldehydes by Merging Visible-Light Photoredox Catalysis and Organophosphorus Chemistry

• Published in: iScience Vol. 6; pp. 102 - 113
• Main Authors: Jiang, Min, Yang, Haijun, Lefebvre, Quentin, Su, Jihu, Fu, Hua
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 31.08.2018; Elsevier
• Subjects: Catalysis; Chemistry; Organic Chemistry; Chemistry; Catalysis; Organic Chemistry
• ISSN: 2589-0042; 2589-0042
• DOI: 10.1016/j.isci.2018.07.011

Carbon-carbon double bond (C=C) formation is a crucial transformation in organic chemistry. Visible-light photoredox catalysis provides economical and sustainable opportunities for the development of novel and peculiar organic reactions. Here we report a method for the olefination of alkyl halides with aldehydes by visible-light photoredox catalysis using triphenylphosphine as a reductive quencher (103 examples). This transformation accommodates a variety of aldehydes including paraformaldehyde; aqueous formaldehyde; 2,2,2-trifluoroacetaldehyde monohydrate; 2,2,2-trifluoro-1-methoxyethanol; and other common aldehydes. The present method exhibits several advantages, including operational simplicity, mild reaction conditions, wide functional group tolerance, and amenability to gram-scale synthesis. We anticipate that it will be widely used in the synthesis of organic molecules, natural products, biological molecules, and polymers. [Display omitted] •General olefination of benzyl halides and bromoacetamides with aldehydes•Operational simplicity and mild conditions under visible-light photoredox catalysis•Wide substrate scope and high efficiency•Amenability to gram-scale synthesis Chemistry; Catalysis; Organic Chemistry